Active compound combinations comprising a (thio)carboxamide derivative and a fungicidal compound

ABSTRACT

The present invention relates to active compound combinations, in particular within a fungicide composition, which comprises (A) a N-cyclopropyl-N-[substituted-benzyl]-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide or thiocarboxamide derivative and a further fungicidally active compound (B). Moreover, the invention relates to a method for curatively or preventively or eradicatively controlling the phytopathogenic fungi of plants or crops, to the use of a combination according to the invention for the treatment of seed, to a method for protecting a seed and not at least to the treated seed.

CROSS-REFERENCE TO RELATED APPLICATION(S)

The present application is a 35 U.S.C. § 371 national phase conversionof PCT/EP2014/072099 filed on Oct. 15, 2014, which claims priority ofEuropean Application No. 13356015.1 filed on Oct. 16, 2013. Applicantsclaim priority to each of the foregoing patent applications. The PCTInternational Application was published in the English language.

FIELD OF THE INVENTION

The present invention relates to active compound combinations, inparticular within a fungicide composition, which comprises (A) aN-cyclopropyl-N-[substituted-benzyl]-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamideor thiocarboxamide derivative and a further fungicidally active compound(B). Moreover, the invention relates to a method for curatively orpreventively or eradicatively controlling the phytopathogenic fungi ofplants or crops, to the use of a combination according to the inventionfor the treatment of seed, to a method for protecting a seed and not atleast to the treated seed.

BACKGROUND OF THE INVENTION

N-cyclopropyl-N-[substituted-benzyl]-carboxamides or thiocarboxamides,their preparation from commercially available materials and their use asfungicides are disclosed in WO2007/087906, WO2009/016220 andWO2010/130767.

N-cyclopropyl-N-[substituted-benzyl]-carboxamides or thiocarboxamides inmixtures with fungicides are disclosed in WO2012/143125. Nevertheless,the synergistic active compound combinations of the present inventionare not disclosed nor suggested.

Since the environmental and economic requirements imposed on modern-daycrop protection compositions are continually increasing, with regard,for example, to the spectrum of action, toxicity, selectivity,application rate, formation of residues, and favourable preparationability, and since, furthermore, there may be problems, for example,with resistances, a constant task is to develop new compositions, inparticular fungicidal agents, which in some areas at least help tofulfil the abovementioned requirements.

The present invention provides active compound combinations/compositionswhich in some aspects at least achieve the stated objective.

SUMMARY OF THE INVENTION

It has now been found, surprisingly, that the combinations according tothe invention not only bring about the additive enhancement of thespectrum of action with respect to the phytopathogen to be controlledthat was in principle to be expected but achieves a synergistic effectwhich extends the range of action of the component (A) and of thecomponent (B) in two ways. Firstly, the rates of application of thecomponent (A) and of the component (B) are lowered whilst the actionremains equally good. Secondly, the combination still achieves a highdegree of phytopathogen control even where the two individual compoundshave become totally ineffective in such a low application rate range.This allows, on the one hand, a substantial broadening of the spectrumof phytopathogens that can be controlled and, on the other hand,increased safety in use.

In addition to the fungicidal synergistic activity, the active compoundcombinations according to the invention have further surprisingproperties which, in a wider sense, may also be called synergistic, suchas, for example: broadening of the activity spectrum to otherphytopathogens, for example to resistant strains of plant diseases;lower application rates of the active compounds; sufficient control ofpests with the aid of the active compound combinations according to theinvention even at application rates where the individual compounds showno or virtually no activity; advantageous behaviour during formulationor during use, for example during grinding, sieving, emulsifying,dissolving or dispensing; improved storage stability and lightstability; advantageous residue formation; improved toxicological orecotoxicological behaviour; improved properties of the plant, forexample better growth, increased harvest yields, a better developed rootsystem, a larger leaf area, greener leaves, stronger shoots, less seedrequired, lower phytotoxicity, mobilization of the defence system of theplant, good compatibility with plants. Thus, the use of the activecompound combinations or compositions according to the inventioncontributes considerably to keeping young cereal stands healthy, whichincreases, for example, the winter survival of the cereal seed treated,and also safeguards quality and yield. Moreover, the active compoundcombinations according to the invention may contribute to enhancedsystemic action. Even if the individual compounds of the combinationhave no sufficient systemic properties, the active compound combinationsaccording to the invention may still have this property. In a similarmanner, the active compound combinations according to the invention mayresult in higher persistency of the fungicidal action.

Accordingly, the present invention provides a combination comprising:

(A) at least one derivative of formula (I)

wherein T represents an oxygen or a sulfur atom and X is selected fromthe list of 2-isopropyl, 2-cyclopropyl, 2-tert-butyl, 5-chloro-2-ethyl,5-chloro-2-isopropyl, 2-ethyl-5-fluoro, 5-fluoro-2-isopropyl,2-cyclopropyl-5-fluoro, 2-cyclopentyl-5-fluoro, 2-fluoro-6-isopropyl,2-ethyl-5-methyl, 2-isopropyl-5-methyl, 2-cyclopropyl-5-methyl,2-tert-butyl-5-methyl, 5-chloro-2-(trifluoromethyl),5-methyl-2-(trifluoromethyl), 2-chloro-6-(trifluoromethyl),3-chloro-2-fluoro-6-(trifluoromethyl) and 2-ethyl-4,5-dimethyl, or anagrochemically acceptable salt thereof,and(B) at least one further active fungicidal compound B selected among thegroup L1 consisting of

-   (b1) Isofetamid;-   (b2)    (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide;-   (b3)    [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol;-   (b4)    (S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol;-   (b5)    (R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol;-   (b6)    2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione;-   (b7)    1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-ylthiocyanate;-   (b8)    5-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole;-   (b9)    2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione;-   (b10)    2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione;-   (b11)    2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione;-   (b12)    1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl    thiocyanate;-   (b13)    1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl    thiocyanate;-   (b14)    5-(allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole;-   (b15)    5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole;-   (b16)    2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione;-   (b17)    2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione;-   (b18)    2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione;-   (b19)    2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,    2,4-triazole-3-thione;-   (b20)    2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione;-   (b21)    2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione;-   (b22)    2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione;-   (b23)    2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione;-   (b24)    2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide;-   (b25) 2-(6-benzylpyridin-2-yl)quinazoline;-   (b26)    2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline;-   (b27)    3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline;-   (b28) Abscisic acid;-   (b29)    3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propan-2-yl]-1H-pyrazole-4-carboxamide;-   (b30)    N′-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide;-   (b31)    N′-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide;-   (b32)    N′-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide;-   (b33)    N′-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide;-   (b34)    N′-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide;-   (b35)    N′-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide;-   (b36)    3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide;-   (b37)    3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide;-   (b38)    3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide;-   (b39)    N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b40)    2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol;-   (b41)    2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;-   (b42)    2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol;-   (b43)    2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;-   (b44)    2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol;-   (b45)    9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine;-   (b46)    2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol;-   (b47)    2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol;-   (b48)    (2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;-   (b49)    (2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;-   (b50)    (2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;-   (b51)    (2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;-   (b52)    (1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopeantanol;-   (b53)    (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol;-   (b54)    4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b55)    4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b56)    4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b57)    4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b58)    N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b59)    4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b60)    4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b61)    4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b62)    N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b63)    4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b64)    4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b65)    4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b66)    N′-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide;-   (b67)    N′-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide;-   (b68)    N′-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide;-   (b69)    N′-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide;-   (b70)    N′-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide;-   (b71)    N′-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide;-   (b72)    N′-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide;-   (b73)    N′-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide;-   (b74)    N′-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide;-   (b75)    N′-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide;-   (b76)    5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol;-   (b77)    2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2    -oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone;-   (b78)    2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)    phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone;-   (b79)    2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone;-   (b80)    2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl    methanesulfonate;-   (b81)    2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl    methanesulfonate;-   (b82)    2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone;-   (b83)    2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone;-   (b84)    2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone;-   (b85)    2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone;-   (b86)    2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone;-   (b87)    2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-    dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone;-   (b88)    2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl    methanesulfonate;-   (b89)    2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl    methanesulfonate;-   (b90)    2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl    methanesulfonate;-   (b91)    2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl    methanesulfonate;-   (b92)    (2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol;-   (b93)    (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol;    with the proviso that, when the derivative of formula (I) is    N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,    then the active fungicidal compound B is not-   (b54)    4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b55)    4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b56)    4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b57)    4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b58)    N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b59)    4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b60) 4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-d    methyl-1H-pyrazol-5-amine;-   (b61)    4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b62)    N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b63)    4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b64)    4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b65) 4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-d    methyl-1H-pyrazol-5-amine;

DETAILED DESCRIPTION OF THE INVENTION

Preference is given to combinations comprising at least one compound ofthe formula (I) selected from the group consisting of:

-   N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide    (compound A1),-   N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide    (compound A2),-   N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide    (compound A3),-   N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide    (compound A4),-   N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide    (compound A5),-   N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide    (compound A6),-   N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide    (compound A7),-   N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide    (compound A8),-   N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide    (compound A9),-   N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide    (compound A10),-   N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide    (compound A11),-   N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide    (compound A12),-   N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide    (compound A13),-   N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide    (compound A14),-   N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide    (compound A15),-   N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide    (compound A16),-   N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide    (compound A17),-   N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide    (compound A18).-   N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide    (compound A19),-   and    N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothio-amide    (compound A20).

In a particular embodiment of the invention, the fungicidal compound Bof the invention is selected from the group L2 consisting of:

-   (b2)    (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide;-   (b29)    3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propan-2-yl]-1H-pyrazole-4-carboxamide;-   (b30)    N′-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide;-   (b31)    N′-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide;-   (b32)    N′-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide;-   (b33)    N′-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide;-   (b34)    N′-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide;-   (b35)    N′-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide;-   (b36)    3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1-methyl-1H-pyrazole-4-carboxamide;-   (b37)    3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide;-   (b38)    3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide;-   (b39)    N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b40)    2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol;-   (b41)    2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;-   (b42)    2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol;-   (b43)    2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;-   (b44)    2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol;-   (b45)    9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine;-   (b46)    2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol;-   (b47)    2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol;-   (b48)    (2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;-   (b49)    (2R)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;-   (b50)    (2S)-2-(1-chlorocyclopropyl)-4-[(1S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;-   (b51)    (2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;-   (b52)    (1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopeantanol;-   (b53)    (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol;-   (b54)    4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b55)    4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b56)    4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b57)    4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b58)    N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b59)    4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b60)    4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b61)    4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b62)    N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b63)    4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b64)    4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b65)    4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine.-   (b66)    N′-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide;-   (b67)    N′-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide;-   (b68)    N′-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide;-   (b69)    N′-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide;-   (b70)    N′-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide;-   (b71)    N′-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide;-   (b72)    N′-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide;-   (b73)    N′-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide;-   (b74)    N′-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide;-   (b75)    N′-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide;-   (b76)    5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol;-   (b77)    2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone;-   (b78)    2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone;-   (b79)    2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone;-   (b80)    2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl    methanesulfonate;-   (b81)    2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl    methanesulfonate;-   (b82)    2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone;-   (b83)    2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone;-   (b84)    2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone;-   (b85)    2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone;-   (b86)    2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5S)-5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone;-   (b87)    2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{(5R)-5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone;-   (b88)    2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl    methanesulfonate;-   (b89)    2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl    methanesulfonate;-   (b90)    2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl    methanesulfonate;-   (b91)    2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl    methanesulfonate;-   (b92)    (2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol;-   (b93)    (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol;    with the proviso that, when the derivative of formula (I) is    N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide,    then the active fungicidal compound B is not-   (b54)    4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b55)    4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b56)    4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b57)    4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b58)    N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b59)    4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b60)    4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b61)    4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b62)    N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b63)    4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b64)    4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b65)    4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine.

In a further particular embodiment of the invention, the fungicidalcompound B of the invention is selected from the group L3 consisting of:

-   (b27) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin 1    yl)quinoline;-   (b29)    3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propan-2-yl]-1H-pyrazole-4-carboxamide;-   (b39)    N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b40)    2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol;-   (b41)    2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;-   (b45)    9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine;-   (b46)    2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol;-   (b47)    2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol.

In another further particular embodiment of the invention, thefungicidal compound B of the invention is selected from the group L4consisting of:

-   (b29)    3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propan-2-yl]-1H-pyrazole-4-carboxamide;-   (b39)    N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine;-   (b40)    2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol;-   (b41)    2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;-   (b45)    9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine;-   (b46)    2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol;-   (b47)    2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol.

All named mixing partners of the groups L1, L2, L3 or L4 can, if theirfunctional groups enable this, optionally form salts with suitable basesor acids.

In a preferred embodiment this invention is directed to a mixturecomprising the compound A1 as compound of formula (I) and one compoundselected from the compounds listed in group L1, L2, L3 or L4, exceptcompound b54, b55, b56, b57, b58, b59, B60, b61, b62, b63, b64 or b65.

In a preferred embodiment this invention is directed to mixturescomprising the compound A2 as compound of formula (I) and one compoundselected from the compounds listed in group L1, L2, L3 or L4.

In a preferred embodiment this invention is directed to mixturescomprising the compound A3 as compound of formula (I) and one compoundselected from the compounds listed in group L1, L2, L3 or L4.

In a preferred embodiment this invention is directed to mixturescomprising the compound A4 as compound of formula (I) and one compoundselected from the compounds listed in group L1, L2, L3 or L4.

In a preferred embodiment this invention is directed to mixturescomprising the compound A5 as compound of formula (I) and one compoundselected from the compounds listed in group L1, L2, L3 or L4.

In a preferred embodiment this invention is directed to mixturescomprising the compound A6 as compound of formula (I) and one compoundselected from the compounds listed in group L1, L2, L3 or L4.

In a preferred embodiment this invention is directed to mixturescomprising the compound A7 as compound of formula (I) and one compoundselected from the compounds listed in group L1, L2, L3 or L4.

In a preferred embodiment this invention is directed to mixturescomprising the compound A8 as compound of formula (I) and one compoundselected from the compounds listed in group L1, L2, L3 or L4.

In a preferred embodiment this invention is directed to mixturescomprising the compound A9 as compound of formula (I) and one compoundselected from the compounds listed in group L1, L2, L3 or L4.

In a preferred embodiment this invention is directed to mixturescomprising the compound A10 as compound of formula (I) and one compoundselected from the compounds listed in group L1, L2, L3 or L4.

In a preferred embodiment this invention is directed to mixturescomprising the compound A11 as compound of formula (I) and one compoundselected from the compounds listed in group L1, L2, L3 or L4.

In a preferred embodiment this invention is directed to mixturescomprising the compound A12 as compound of formula (I) and one compoundselected from the compounds listed in group L1, L2, L3 or L4.

In a preferred embodiment this invention is directed to mixturescomprising the compound A13 as compound of formula (I) and one compoundselected from the compounds in group L1, L2, L3 or L4.

In a preferred embodiment this invention is directed to mixturescomprising the compound A14 as compound of formula (I) and one compoundselected from the compounds in group L1, L2, L3 or L4.

In a preferred embodiment this invention is directed to mixturescomprising the compound A15 as compound of formula (I) and one compoundselected from the compounds listed in group L1, L2, L3 or L4.

In a preferred embodiment this invention is directed to mixturescomprising the compound A16 as compound of formula (I) and one compoundselected from the compounds listed in group L1, L2, L3 or L4.

In a preferred embodiment this invention is directed to mixturescomprising the compound A17 as compound of formula (I) and one compoundselected from the compounds in group L1, L2, L3 or L4.

In a preferred embodiment this invention is directed to mixturescomprising the compound A18 as compound of formula (I) and one compoundselected from the compounds listed in group L1, L2, L3 or L4.

In a preferred embodiment this invention is directed to mixturescomprising the compound A19 as compound of formula (I) and one compoundselected from the compounds in group L1, L2, L3 or L4.

In a preferred embodiment this invention is directed to mixturescomprising the compound A20 as compound of formula (I) and one compoundselected from the compounds in group L1, L2, L3 or L4.

If the active compounds in the active compound combinations according tothe invention are present in certain weight ratios, the synergisticeffect is particularly pronounced. However, the weight ratios of theactive compounds in the active compound combinations can be variedwithin a relatively wide range.

In the combinations according to the invention the compounds (A) and (B)are present in a synergistically effective weight ratio of A:B in arange of 1000:1 to 1:1000, preferably in a weight ratio of 100:1 to1:100, more preferably in a weight ratio of 50:1 to 1:50, even morepreferably in a weight ratio of 20:1 to 1:20. Further ratios of A:Bwhich can be used according to the present invention with increasingpreference in the order given are: 95:1 to 1:95, 90:1 to 1:90, 85:1 to1:85, 80:1 to 1:80, 75:1 to 1:75, 70:1 to 1:70, 65:1 to 1:65, 60:1 to1:60, 55:1 to 1:55, 45:1 to 1:45, 40:1 to 1:40, 35:1 to 1:35, 30:1 to1:30, 25:1 to 1:25, 15:1 to 1:15, 10:1 to 1:10, 5:1 to 1:5, 4:1 to 1:4,3:1 to 1:3, 2:1 to 1:2.

Where a compound (A) or a compound (B) can be present in tautomericform, such a compound is understood hereinabove and hereinbelow also toinclude, where applicable, corresponding tautomeric forms, even whenthese are not specifically mentioned in each case.

Compounds (A) or compounds (B) having at least one basic centre arecapable of forming, for example, acid addition salts, e.g. with stronginorganic acids, such as mineral acids, e.g. perchloric acid, sulfuricacid, nitric acid, nitrous acid, a phosphoric acid or a hydrohalic acid,with strong organic carboxylic acids, such as unsubstituted substituted,e.g. halo-substituted, C₁-C₄-alkanecarboxylic acids, e.g. acetic acid,saturated or unsaturated dicarboxylic acids, e.g. oxalic, malonic,succinic, maleic, fumaric and phthalic acid, hydroxycarboxylic acids,e.g. ascorbic, lactic, malic, tartaric and citric acid, or benzoic acid,or with organic sulfonic acids, such as unsubstituted or substituted,e.g. halo-substituted, C₁-C₄-alkane- or arylsulfonic acids, e.g.methane- or p-toluene-sulfonic acid. Compounds (A) or compounds (B)having at least one acid group are capable of forming, for example,salts with bases, e.g. metal salts, such as alkali metal or alkalineearth metal salts, e.g. sodium, potassium or magnesium salts, or saltswith ammonia or an organic amine, such as morpholine, piperidine,pyrrolidine, a mono-, di- or tri-lower alkylamine, e.g. ethyl-,diethyl-, triethyl- or dimethylpropyl-amine, or a mono-, di- ortri-hydroxy-lower alkylamine, e.g. mono-, di- or tri-ethanolamine. Inaddition, corresponding internal salts may optionally be formed. In thecontext of the invention, preference is given to agrochemicallyadvantageous salts. In view of the close relationship between thecompounds (A) or the compounds (B) in free form and in the form of theirsalts, hereinabove and herein below any reference to the free compounds(A) or free compounds (B) or to their salts should be understood asincluding also the corresponding salts or the free compounds (A) or freecompounds (B), respectively, where appropriate and expedient. Theequivalent also applies to tautomers of compounds (A) or compounds (B)and to their salts.

According to the invention the expression “combination” stands for thevarious combinations of compounds (A) and (B), for example in a single“ready-mix” form, in a combined spray mixture composed from separateformulations of the single active compounds, such as a “tank-mix”, andin a combined use of the single active ingredients when applied in asequential manner, i.e. one after the other with a reasonably shortperiod, such as a few hours or days. Preferably the order of applyingthe compounds (A) and (B) is not essential for working the presentinvention.

The present invention furthermore relates to compositions forcombating/controlling undesirable microorganisms comprising the activecompound combinations according to the invention. Preferably, thecompositions are fungicidal compositions comprising agriculturallysuitable auxiliaries, solvents, carriers, surfactants or extenders.

Furthermore the invention relates to a method of combating undesirablemicroorganisms, characterized in that the active compound combinationsaccording to the invention are applied to the phytopathogenic fungiand/or their habitat.

According to the invention, carrier is to be understood as meaning anatural or synthetic, organic or inorganic substance which is mixed orcombined with the active compounds for better applicability, inparticular for application to plants or plant parts or seeds. Thecarrier, which may be solid or liquid, is generally inert and should besuitable for use in agriculture.

Suitable solid or liquid carriers are: for example ammonium salts andnatural ground minerals, such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals, such as finely divided silica, alumina and natural orsynthetic silicates, resins, waxes, solid fertilizers, water, alcohols,especially butanol, organic solvents, mineral oils and vegetable oils,and also derivatives thereof. It is also possible to use mixtures ofsuch carriers. Solid carriers suitable for granules are: for examplecrushed and fractionated natural minerals, such as calcite, marble,pumice, sepiolite, dolomite, and also synthetic granules of inorganicand organic meals and also granules of organic material, such assawdust, coconut shells, maize cobs and tobacco stalks.

Suitable liquefied gaseous extenders or carriers are liquids which aregaseous at ambient temperature and under atmospheric pressure, forexample aerosol propellants, such as butane, propane, nitrogen andcarbon dioxide.

Tackifiers, such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules and latices, such as gumarabic, polyvinyl alcohol, polyvinyl acetate, or else naturalphospholipids, such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other possible additivesare mineral and vegetable oils and waxes, optionally modified.

If the extender used is water, it is also possible for example, to useorganic solvents as auxiliary solvents. Suitable liquid solvents areessentially: aromatic compounds, such as xylene, toluene oralkylnaphthalenes, chlorinated aromatic compounds or chlorinatedaliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes ormethylene chloride, aliphatic hydrocarbons, such as cyclohexane orparaffins, for example mineral oil fractions, mineral and vegetableoils, alcohols, such as butanol or glycol, and also ethers and estersthereof, ketones, such as acetone, methyl ethyl ketone, methyl isobutylketone or cyclohexanone, strongly polar solvents, such asdimethylformamide and dimethyl sulfoxide, and also water.

The compositions according to the invention may comprise additionalfurther components, such as, for example, surfactants. Suitablesurfactants are emulsifiers, dispersants or wetting agents having ionicor nonionic properties, or mixtures of these surfactants. Examples ofthese are salts of polyacrylic acid, salts of lignosulfonic acid, saltsof phenolsulfonic acid or naphthalenesulfonic acid, polycondensates ofethylene oxide with fatty alcohols or with fatty acids or with fattyamines, substituted phenols (preferably alkylphenols or arylphenols),salts of sulfosuccinic esters, taurine derivatives (preferably alkyltaurates), phosphoric esters of polyethoxylated alcohols or phenols,fatty esters of polyols, and derivatives of the compounds containingsulfates, sulfonates and phosphates. The presence of a surfactant isrequired if one of the active compounds and/or one of the inert carriersis insoluble in water and when the application takes place in water. Theproportion of surfactants is between 5 and 40 percent by weight of thecomposition according to the invention.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide, Prussian blue, and organic dyes, such asalizarin dyes, azo dyes and metal phthalocyanine dyes, and tracenutrients, such as salts of iron, manganese, boron, copper, cobalt,molybdenum and zinc.

If appropriate, other additional components may also be present, forexample protective colloids, binders, adhesives, thickeners, thixotropicsubstances, penetrants, stabilizers, sequestering agents, complexformers. In general, the active compounds can be combined with any solidor liquid additive customarily used for formulation purposes.

In general, the compositions according to the invention comprise between0.05 and 99 percent by weight, 0.01 and 98 percent by weight, preferablebetween 0.1 and 95 percent by weight, particularly preferred between 0.5and 90 percent by weight of the active compound combination according tothe invention, very particularly preferable between 10 and 70 percent byweight.

The active compound combinations or compositions according to theinvention can be used as such or, depending on their respective physicaland/or chemical properties, in the form of their formulations or the useforms prepared therefrom, such as aerosols, capsule suspensions,cold-fogging concentrates, warm-fogging concentrates, encapsulatedgranules, fine granules, flowable concentrates for the treatment ofseed, ready-to-use solutions, dustable powders, emulsifiableconcentrates, oil-in-water emulsions, water-in-oil emulsions,macrogranules, microgranules, oil-dispersible powders, oil-miscibleflowable concentrates, oil-miscible liquids, foams, pastes,pesticide-coated seed, suspension concentrates, suspoemulsionconcentrates, soluble concentrates, suspensions, wettable powders,soluble powders, dusts and granules, water-soluble granules or tablets,water-soluble powders for the treatment of seed, wettable powders,natural products and synthetic substances impregnated with activecompound, and also microencapsulations in polymeric substances and incoating materials for seed, and also ULV cold-fogging and warm-foggingformulations.

The formulations mentioned can be prepared in a manner known per se, forexample by mixing the active compounds or the active compoundcombinations with at least one additive. Suitable additives are allcustomary formulation auxiliaries, such as, for example, organicsolvents, extenders, solvents or diluents, solid carriers and fillers,surfactants (such as adjuvants, emulsifiers, dispersants, protectivecolloids, wetting agents and tackifiers), dispersants and/or binders orfixatives, preservatives, dyes and pigments, defoamers, inorganic andorganic thickeners, water repellents, if appropriate siccatives and UVstabilizers, gibberellins and also water and further processingauxiliaries. Depending on the formulation type to be prepared in eachcase, further processing steps such as, for example, wet grinding, drygrinding or granulation may be required.

The compositions according to the invention do not only compriseready-to-use compositions which can be applied with suitable apparatusto the plant or the seed, but also commercial concentrates which have tobe diluted with water prior to use.

The active compound combinations according to the invention can bepresent in (commercial) formulations and in the use forms prepared fromthese formulations as a mixture with other (known) active compounds,such as insecticides, attractants, sterilants, bactericides, acaricides,nematicides, fungicides, growth regulators, herbicides, fertilizers,safeners and Semiochemicals.

The treatment according to the invention of the plants and plant partswith the active compounds or compositions is carried out directly or byaction on their surroundings, habitat or storage space using customarytreatment methods, for example by dipping, spraying, atomizing,irrigating, evaporating, dusting, fogging, broadcasting, foaming,painting, spreading-on, watering (drenching), drip irrigating and, inthe case of propagation material, in particular in the case of seeds,furthermore as a powder for dry seed treatment, a solution for seedtreatment, a water-soluble powder for slurry treatment, by incrusting,by coating with one or more layers, etc. It is furthermore possible toapply the active compounds by the ultra-low volume method, or to injectthe active compound preparation or the active compound itself into thesoil.

The invention furthermore comprises a method for treating seed. Theinvention furthermore relates to seed treated according to one of themethods described in the preceding paragraph.

The active compounds or compositions according to the invention areespecially suitable for treating seed. A large part of the damage tocrop plants caused by harmful organisms is triggered by an infection ofthe seed during storage or after sowing as well as during and aftergermination of the plant. This phase is particularly critical since theroots and shoots of the growing plant are particularly sensitive, andeven small damage may result in the death of the plant. Accordingly,there is great interest in protecting the seed and the germinating plantby using appropriate compositions.

The control of phytopathogenic fungi by treating the seed of plants hasbeen known for a long time and is the subject of continuousimprovements. However, the treatment of seed entails a series ofproblems which cannot always be solved in a satisfactory manner. Thus,it is desirable to develop methods for protecting the seed and thegerminating plant which dispense with the additional application of cropprotection agents after sowing or after the emergence of the plants orwhich at least considerably reduce additional application. It isfurthermore desirable to optimize the amount of active compound employedin such a way as to provide maximum protection for the seed and thegerminating plant from attack by phytopathogenic fungi, but withoutdamaging the plant itself by the active compound employed. Inparticular, methods for the treatment of seed should also take intoconsideration the intrinsic fungicidal properties of transgenic plantsin order to achieve optimum protection of the seed and the germinatingplant with a minimum of crop protection agents being employed.

Accordingly, the present invention also relates in particular to amethod for protecting seed and germinating plants against attack byphytopathogenic fungi by treating the seed with a composition accordingto the invention. The invention also relates to the use of thecompositions according to the invention for treating seed for protectingthe seed and the germinating plant against phytopathogenic fungi.Furthermore, the invention relates to seed treated with a compositionaccording to the invention for protection against phytopathogenic fungi.

The control of phytopathogenic fungi which damage plants post-emergenceis carried out primarily by treating the soil and the above-ground partsof plants with crop protection compositions. Owing to the concernsregarding a possible impact of the crop protection composition on theenvironment and the health of humans and animals, there are efforts toreduce the amount of active compounds applied.

One of the advantages of the present invention is that, because of theparticular systemic properties of the compositions according to theinvention, treatment of the seed with these compositions not onlyprotects the seed itself, but also the resulting plants after emergence,from phytopathogenic fungi. In this manner, the immediate treatment ofthe crop at the time of sowing or shortly thereafter can be dispensedwith.

It is also considered to be advantageous that the mixtures according tothe invention can be used in particular also for transgenic seed wherethe plant growing from this seed is capable of expressing a proteinwhich acts against pests. By treating such seed with the active compoundcombinations or compositions according to the invention, even by theexpression of the, for example, insecticidal protein, certain pests maybe controlled. Surprisingly, a further synergistic effect may beobserved here, which additionally increases the effectiveness of theprotection against attack by pests.

The compositions according to the invention are suitable for protectingseed of any plant variety employed in agriculture, in the greenhouse, inforests or in horticulture or viticulture. In particular, this takes theform of seed of cereals (such as wheat, barley, rye, triticale, millet,oats), maize (corn), cotton, soya bean, rice, potatoes, sunflowers,beans, coffee, beets (e.g. sugar beets and fodder beets), peanuts,oilseed rape, poppies, olives, coconuts, cacao, sugar cane, tobacco,vegetables (such as tomatoes, cucumbers, onions and lettuce), lawn andornamental plants (also see below). The treatment of seeds of cereals(such as wheat, barley, rye, triticale, and oats), maize (corn) and riceis of particular importance.

According to the invention all plants and plant parts can be treated. Byplants is meant all plants and plant populations such as desirable andundesirable wild plants, cultivars and plant varieties (whether or notprotectable by plant variety or plant breeder's rights). Cultivars andplant varieties can be plants obtained by conventional propagation andbreeding methods which can be assisted or supplemented by one or morebiotechnological methods such as by use of double haploids, protoplastfusion, random and directed mutagenesis, molecular or genetic markers orby bioengineering and genetic engineering methods. By plant parts ismeant all above ground and below ground parts and organs of plants suchas shoot, leaf, blossom and root, whereby for example leaves, needles,stems, branches, blossoms, fruiting bodies, fruits and seed as well asroots, corms and rhizomes are listed. Crops and vegetative andgenerative propagating material, for example cuttings, corms, rhizomes,runners and seeds also belong to plant parts.

Among the plants that can be protected by the method according to theinvention, mention may be made of major field crops like corn, soybean,cotton, Brassica oilseeds such as Brassica napus (e.g. canola), Brassicarapa, B. juncea (e.g. mustard) and Brassica carinata, rice, wheat,sugarbeet, sugarcane, oats, rye, barley, millet, triticale, flax, vineand various fruits and vegetables of various botanical taxa such asRosaceae sp. (for instance pip fruit such as apples and pears, but alsostone fruit such as apricots, cherries, almonds and peaches, berryfruits such as strawberries), Ribesioidae sp., Juglandaceae sp.,Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceaesp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for instance bananatrees and plantings), Rubiaceae sp. (for instance coffee), Theaceae sp.,Sterculiceae sp., Rutaceae sp. (for instance lemons, oranges andgrapefruit); Solanaceae sp. (for instance tomatoes, potatoes, peppers,eggplant), Liliaceae sp., Compositiae sp. (for instance lettuce,artichoke and chicory—including root chicory, endive or common chicory),Umbelliferae sp. (for instance carrot, parsley, celery and celeriac),Cucurbitaceae sp. (for instance cucumber—including pickling cucumber,squash, watermelon, gourds and melons), Alliaceae sp. (for instanceonions and leek), Cruciferae sp. (for instance white cabbage, redcabbage, broccoli, cauliflower, brussel sprouts, pak choi, kohlrabi,radish, horseradish, cress, Chinese cabbage), Leguminosae sp. (forinstance peanuts, peas and beans beans—such as climbing beans and broadbeans), Chenopodiaceae sp. (for instance mangold, spinach beet, spinach,beetroots), Malvaceae (for instance okra), Asparagaceae (for instanceasparagus); horticultural and forest crops; ornamental plants; as wellas genetically modified homologues of these crops.

The method of treatment according to the invention can be used in thetreatment of genetically modified organisms (GMOs), e.g. plants orseeds. Genetically modified plants (or transgenic plants) are plants ofwhich a heterologous gene has been stably integrated into genome. Theexpression “heterologous gene” essentially means a gene which isprovided or assembled outside the plant and when introduced in thenuclear, chloroplastic or mitochondrial genome gives the transformedplant new or improved agronomic or other properties by expressing aprotein or polypeptide of interest or by downregulating or silencingother gene(s) which are present in the plant (using for example,antisense technology, cosuppression technology or RNAinterference—RNAi—technology). A heterologous gene that is located inthe genome is also called a transgene. A transgene that is defined byits particular location in the plant genome is called a transformationor transgenic event.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the active compounds and compositions which can be usedaccording to the invention, better plant growth, increased tolerance tohigh or low temperatures, increased tolerance to drought or to water orsoil salt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, bigger fruits, largerplant height, greener leaf color, earlier flowering, higher qualityand/or a higher nutritional value of the harvested products, highersugar concentration within the fruits, better storage stability and/orprocessability of the harvested products are possible, which exceed theeffects which were actually to be expected.

At certain application rates, the active compound combinations accordingto the invention may also have a strengthening effect in plants.Accordingly, they are also suitable for mobilizing the defense system ofthe plant against attack by unwanted microorganisms. This may, ifappropriate, be one of the reasons of the enhanced activity of thecombinations according to the invention, for example against fungi.Plant-strengthening (resistance-inducing) substances are to beunderstood as meaning, in the present context, those substances orcombinations of substances which are capable of stimulating the defensesystem of plants in such a way that, when subsequently inoculated withunwanted microorganisms, the treated plants display a substantial degreeof resistance to these microorganisms. In the present case, unwantedmicroorganisms are to be understood as meaning phytopathogenic fungi,bacteria and viruses. Thus, the substances according to the inventioncan be employed for protecting plants against attack by theabovementioned pathogens within a certain period of time after thetreatment. The period of time within which protection is effectedgenerally extends from 1 to 10 days, preferably 1 to 7 days, after thetreatment of the plants with the active compounds.

Plants and plant cultivars which are preferably to be treated accordingto the invention include all plants which have genetic material whichimpart particularly advantageous, useful traits to these plants (whetherobtained by breeding and/or biotechnological means).

Plants and plant cultivars which are also preferably to be treatedaccording to the invention are resistant against one or more bioticstresses, i.e. said plants show a better defense against animal andmicrobial pests, such as against nematodes, insects, mites,phytopathogenic fungi, bacteria, viruses and/or viroids. Examples ofnematode resistant plants are described in e.g. U.S. patent applicationSer. Nos. 11/765,491, 11/765,494, 10/926,819, 10/782,020, 12/032,479,10/783,417, 10/782,096, 11/657,964, 12/192,904, 11/396,808, 12/166,253,12/166,239, 12/166,124, 12/166,209, 11/762,886, 12/364,335, 11/763,947,12/252,453, 12/209,354, 12/491,396 or 12/497,221.

Plants and plant cultivars which may also be treated according to theinvention are those plants which are resistant to one or more abioticstresses. Abiotic stress conditions may include, for example, drought,cold temperature exposure, heat exposure, osmotic stress, flooding,increased soil salinity, increased mineral exposure, ozone exposure,high light exposure, limited availability of nitrogen nutrients, limitedavailability of phosphorus nutrients, shade avoidance.

Plants and plant cultivars which may also be treated according to theinvention, are those plants characterized by enhanced yieldcharacteristics. Increased yield in said plants can be the result of,for example, improved plant physiology, growth and development, such aswater use efficiency, water retention efficiency, improved nitrogen use,enhanced carbon assimilation, improved photosynthesis, increasedgermination efficiency and accelerated maturation. Yield can furthermorebe affected by improved plant architecture (under stress and non-stressconditions), including but not limited to, early flowering, floweringcontrol for hybrid seed production, seedling vigor, plant size,internode number and distance, root growth, seed size, fruit size, podsize, pod or ear number, seed number per pod or ear, seed mass, enhancedseed filling, reduced seed dispersal, reduced pod dehiscence and lodgingresistance. Further yield traits include seed composition, such ascarbohydrate content, protein content, oil content and composition,nutritional value, reduction in anti-nutritional compounds, improvedprocessability and better storage stability.

Plants that may be treated according to the invention are hybrid plantsthat already express the characteristic of heterosis or hybrid vigorwhich results in generally higher yield, vigor, health and resistancetowards biotic and abiotic stresses). Such plants are typically made bycrossing an inbred male-sterile parent line (the female parent) withanother inbred male-fertile parent line (the male parent). Hybrid seedis typically harvested from the male sterile plants and sold to growers.Male sterile plants can sometimes (e.g. in corn) be produced bydetasseling, i.e. the mechanical removal of the male reproductive organs(or males flowers) but, more typically, male sterility is the result ofgenetic determinants in the plant genome. In that case, and especiallywhen seed is the desired product to be harvested from the hybrid plantsit is typically useful to ensure that male fertility in the hybridplants is fully restored. This can be accomplished by ensuring that themale parents have appropriate fertility restorer genes which are capableof restoring the male fertility in hybrid plants that contain thegenetic determinants responsible for male-sterility. Geneticdeterminants for male sterility may be located in the cytoplasm.Examples of cytoplasmic male sterility (CMS) were for instance describedin Brassica species (WO 92/05251, WO 95/09910, WO 98/27806, WO05/002324, WO 06/021972 and U.S. Pat. No. 6,229,072). However, geneticdeterminants for male sterility can also be located in the nucleargenome. Male sterile plants can also be obtained by plant biotechnologymethods such as genetic engineering. A particularly useful means ofobtaining male-sterile plants is described in WO 89/10396 in which, forexample, a ribonuclease such as barnase is selectively expressed in thetapetum cells in the stamens. Fertility can then be restored byexpression in the tapetum cells of a ribonuclease inhibitor such asbarstar (e.g. WO 91/02069).

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may be treated according to the inventionare herbicide-tolerant plants, i.e. plants made tolerant to one or moregiven herbicides. Such plants can be obtained either by genetictransformation, or by selection of plants containing a mutationimparting such herbicide tolerance.

Herbicide-resistant plants are for example glyphosate-tolerant plants,i.e. plants made tolerant to the herbicide glyphosate or salts thereof.Plants can be made tolerant to glyphosate through different means. Forexample, glyphosate-tolerant plants can be obtained by transforming theplant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphatesynthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutantCT7) of the bacterium Salmonella typhimurium (Comai et al., 1983,Science 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp.(Barry et al., 1992, Curr. Topics Plant Physiol. 7, 139-145), the genesencoding a Petunia EPSPS (Shah et al., 1986, Science 233, 478-481), aTomato EPSPS (Gasser et al., 1988, J. Biol. Chem. 263, 4280-4289), or anEleusine EPSPS (WO 01/66704). It can also be a mutated EPSPS asdescribed in for example EP 0837944, WO 00/66746, WO 00/66747 or WO02/26995. Glyphosate-tolerant plants can also be obtained by expressinga gene that encodes a glyphosate oxido-reductase enzyme as described inU.S. Pat. Nos. 5,776,760 and 5,463,175. Glyphosate-tolerant plants canalso be obtained by expressing a gene that encodes a glyphosate acetyltransferase enzyme as described in for example WO 02/36782, WO03/092360, WO 05/012515 and WO 07/024782. Glyphosate-tolerant plants canalso be obtained by selecting plants containing naturally-occurringmutations of the above-mentioned genes, as described in for example WO01/024615 or WO 03/013226. Plants expressing EPSPS genes that conferglyphosate tolerance are described in e.g. U.S. patent application Ser.Nos. 11/517,991, 10/739,610, 12/139,408, 12/352,532, 11/312,866,11/315,678, 12/421,292, 11/400,598, 11/651,752, 11/681,285, 11/605,824,12/468,205, 11/760,570, 11/762,526, 11/769,327, 11/769,255, 11/943,801or 12/362,774. Plants comprising other genes that confer glyphosatetolerance, such as decarboxylase genes, are described in e.g. U.S.patent application Ser. Nos. 11/588,811, 11/185,342, 12/364,724,11/185,560 or 12/423,926.

Other herbicide resistant plants are for example plants that are madetolerant to herbicides inhibiting the enzyme glutamine synthase, such asbialaphos, phosphinothricin or glufosinate. Such plants can be obtainedby expressing an enzyme detoxifying the herbicide or a mutant glutaminesynthase enzyme that is resistant to inhibition, e.g. described in U.S.patent application Ser. No. 11/760,602. One such efficient detoxifyingenzyme is an enzyme encoding a phosphinothricin acetyltransferase (suchas the bar or pat protein from Streptomyces species). Plants expressingan exogenous phosphinothricin acetyltransferase are for exampledescribed in U.S. Pat. Nos. 5,561,236; 5,648,477; 5,646,024; 5,273,894;5,637,489; 5,276,268; 5,739,082; 5,908,810 and 7,112,665.

Further herbicide-tolerant plants are also plants that are made tolerantto the herbicides inhibiting the enzyme hydroxyphenylpyruvatedioxygenase(HPPD). Hydroxyphenylpyruvatedioxygenases are enzymes that catalyze thereaction in which para-hydroxyphenylpyruvate (HPP) is transformed intohomogentisate. Plants tolerant to HPPD-inhibitors can be transformedwith a gene encoding a naturally-occurring resistant HPPD enzyme, or agene encoding a mutated or chimeric HPPD enzyme as described in WO96/38567, WO 99/24585, WO 99/24586, WO 2009/144079, WO 2002/046387, orU.S. Pat. No. 6,768,044. Tolerance to HPPD-inhibitors can also beobtained by transforming plants with genes encoding certain enzymesenabling the formation of homogentisate despite the inhibition of thenative HPPD enzyme by the HPPD-inhibitor. Such plants and genes aredescribed in WO 99/34008 and WO 02/36787. Tolerance of plants to HPPDinhibitors can also be improved by transforming plants with a geneencoding an enzyme having prephenate deshydrogenase (PDH) activity inaddition to a gene encoding an HPPD-tolerant enzyme, as described in WO2004/024928. Further, plants can be made more tolerant to HPPD-inhibitorherbicides by adding into their genome a gene encoding an enzyme capableof metabolizing or degrading HPPD inhibitors, such as the CYP450 enzymesshown in WO 2007/103567 and WO 2008/150473.

Still further herbicide resistant plants are plants that are madetolerant to acetolactate synthase (ALS) inhibitors. Known ALS-inhibitorsinclude, for example, sulfonylurea, imidazolinone, triazolopyrimidines,pryimidinyoxy(thio)benzoates, and/or sulfonylaminocarbonyltriazolinoneherbicides. Different mutations in the ALS enzyme (also known asacetohydroxyacid synthase, AHAS) are known to confer tolerance todifferent herbicides and groups of herbicides, as described for examplein Tranel and Wright (2002, Weed Science 50:700-712), but also, in U.S.Pat. Nos. 5,605,011, 5,378,824, 5,141,870, and 5,013,659. The productionof sulfonylurea-tolerant plants and imidazolinone-tolerant plants isdescribed in U.S. Pat. Nos. 5,605,011; 5,013,659; 5,141,870; 5,767,361;5,731,180; 5,304,732; 4,761,373; 5,331,107; 5,928,937; and 5,378,824;and international publication WO 96/33270. Other imidazolinone-tolerantplants are also described in for example WO 2004/040012, WO 2004/106529,WO 2005/020673, WO 2005/093093, WO 2006/007373, WO 2006/015376, WO2006/024351, and WO 2006/060634. Further sulfonylurea- andimidazolinone-tolerant plants are also described in for example WO07/024782 and U.S. Patent Application No. 61/288,958.

Other plants tolerant to imidazolinone and/or sulfonylurea can beobtained by induced mutagenesis, selection in cell cultures in thepresence of the herbicide or mutation breeding as described for examplefor soybeans in U.S. Pat. No. 5,084,082, for rice in WO 97/41218, forsugar beet in U.S. Pat. No. 5,773,702 and WO 99/057965, for lettuce inU.S. Pat. No. 5,198,599, or for sunflower in WO 01/065922.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are insect-resistant transgenic plants, i.e. plants maderesistant to attack by certain target insects. Such plants can beobtained by genetic transformation, or by selection of plants containinga mutation imparting such insect resistance.

An “insect-resistant transgenic plant”, as used herein, includes anyplant containing at least one transgene comprising a coding sequenceencoding:

-   -   1) an insecticidal crystal protein from Bacillus thuringiensis        or an insecticidal portion thereof, such as the insecticidal        crystal proteins listed by Crickmore et al. (1998, Microbiology        and Molecular Biology Reviews, 62: 807-813), updated by        Crickmore et al. (2005) at the Bacillus thuringiensis toxin        nomenclature, online at:    -   http://www(dot)lifesci(dot)sussex(dot)ac(dot)uk/Home/Neil_Crickmore/Bt/),        or insecticidal portions thereof, e.g., proteins of the Cry        protein classes Cry1Ab, Cry1Ac, Cry1B, Cry1C, Cry1D, Cry1F,        Cry2Ab, Cry3Aa, or Cry3Bb or insecticidal portions thereof (e.g.        EP 1999141 and WO 2007/107302), or such proteins encoded by        synthetic genes as e.g. described in and U.S. patent application        Ser. No. 12/249,016; or    -   2) a crystal protein from Bacillus thuringiensis or a portion        thereof which is insecticidal in the presence of a second other        crystal protein from Bacillus thuringiensis or a portion        thereof, such as the binary toxin made up of the Cry34 and Cry35        crystal proteins (Moellenbeck et al. 2001, Nat. Biotechnol. 19:        668-72; Schnepf et al. 2006, Applied Environm. Microbiol. 71,        1765-1774) or the binary toxin made up of the Cry1A or Cry1F        proteins and the Cry2Aa or Cry2Ab or Cry2Ae proteins (U.S.        patent application Ser. No. 12/214,022 and EP 08010791.5); or    -   3) a hybrid insecticidal protein comprising parts of different        insecticidal crystal proteins from Bacillus thuringiensis, such        as a hybrid of the proteins of 1) above or a hybrid of the        proteins of 2) above, e.g., the Cry1A.105 protein produced by        corn event MON89034 (WO 2007/027777); or    -   4) a protein of any one of 1) to 3) above wherein some,        particularly 1 to 10, amino acids have been replaced by another        amino acid to obtain a higher insecticidal activity to a target        insect species, and/or to expand the range of target insect        species affected, and/or because of changes introduced into the        encoding DNA during cloning or transformation, such as the        Cry3Bb1 protein in corn events MON863 or MON88017, or the Cry3A        protein in corn event MIR604; or    -   5) an insecticidal secreted protein from Bacillus thuringiensis        or Bacillus cereus, or an insecticidal portion thereof, such as        the vegetative insecticidal (VIP) proteins listed at:    -   http://www(dot)lifesci(dot)sussex(dot)ac(dot)uk/home/Neil_Crickmore/Bt/vip(dot)html,        e.g., proteins from the VIP3Aa protein class; or    -   6) a secreted protein from Bacillus thuringiensis or Bacillus        cereus which is insecticidal in the presence of a second        secreted protein from Bacillus thuringiensis or B. cereus, such        as the binary toxin made up of the VIP1A and VIP2A proteins (WO        94/21795); or    -   7) a hybrid insecticidal protein comprising parts from different        secreted proteins from Bacillus thuringiensis or Bacillus        cereus, such as a hybrid of the proteins in 1) above or a hybrid        of the proteins in 2) above; or    -   8) a protein of any one of 5) to 7) above wherein some,        particularly 1 to 10, amino acids have been replaced by another        amino acid to obtain a higher insecticidal activity to a target        insect species, and/or to expand the range of target insect        species affected, and/or because of changes introduced into the        encoding DNA during cloning or transformation (while still        encoding an insecticidal protein), such as the VIP3Aa protein in        cotton event COT102; or    -   9) a secreted protein from Bacillus thuringiensis or Bacillus        cereus which is insecticidal in the presence of a crystal        protein from Bacillus thuringiensis, such as the binary toxin        made up of VIP3 and Cry1A or Cry1F (U.S. Patent Appl. No.        61/126,083 and 61/195019), or the binary toxin made up of the        VIP3 protein and the Cry2Aa or Cry2Ab or Cry2Ae proteins (U.S.        patent application Ser. No. 12/214,022 and EP 08010791.5).    -   10) a protein of 9) above wherein some, particularly 1 to 10,        amino acids have been replaced by another amino acid to obtain a        higher insecticidal activity to a target insect species, and/or        to expand the range of target insect species affected, and/or        because of changes introduced into the encoding DNA during        cloning or transformation (while still encoding an insecticidal        protein)

Of course, an insect-resistant transgenic plant, as used herein, alsoincludes any plant comprising a combination of genes encoding theproteins of any one of the above classes 1 to 10. In one embodiment, aninsect-resistant plant contains more than one transgene encoding aprotein of any one of the above classes 1 to 10, to expand the range oftarget insect species affected when using different proteins directed atdifferent target insect species, or to delay insect resistancedevelopment to the plants by using different proteins insecticidal tothe same target insect species but having a different mode of action,such as binding to different receptor binding sites in the insect.

An “insect-resistant transgenic plant”, as used herein, further includesany plant containing at least one transgene comprising a sequenceproducing upon expression a double-stranded RNA which upon ingestion bya plant insect pest inhibits the growth of this insect pest, asdescribed e.g. in WO 2007/080126, WO 2006/129204, WO 2007/074405, WO2007/080127 and WO 2007/035650.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention are tolerant to abiotic stresses. Such plants can be obtainedby genetic transformation, or by selection of plants containing amutation imparting such stress resistance. Particularly useful stresstolerance plants include:

-   -   1) plants which contain a transgene capable of reducing the        expression and/or the activity of poly(ADP-ribose) polymerase        (PARP) gene in the plant cells or plants as described in WO        00/04173, WO/2006/045633, EP 04077984.5, or EP 06009836.5.    -   2) plants which contain a stress tolerance enhancing transgene        capable of reducing the expression and/or the activity of the        PARG encoding genes of the plants or plants cells, as described        e.g. in WO 2004/090140.    -   3) plants which contain a stress tolerance enhancing transgene        coding for a plant-functional enzyme of the nicotineamide        adenine dinucleotide salvage synthesis pathway including        nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic        acid mononucleotide adenyl transferase, nicotinamide adenine        dinucleotide synthetase or nicotine amide        phosphorybosyltransferase as described e.g. in EP 04077624.7, WO        2006/133827, PCT/EP07/002433, EP 1999263, or WO 2007/107326.

Plants or plant cultivars (obtained by plant biotechnology methods suchas genetic engineering) which may also be treated according to theinvention show altered quantity, quality and/or storage-stability of theharvested product and/or altered properties of specific ingredients ofthe harvested product such as:

-   -   1) transgenic plants which synthesize a modified starch, which        in its physical-chemical characteristics, in particular the        amylose content or the amylose/amylopectin ratio, the degree of        branching, the average chain length, the side chain        distribution, the viscosity behaviour, the gelling strength, the        starch grain size and/or the starch grain morphology, is changed        in comparison with the synthesised starch in wild type plant        cells or plants, so that this is better suited for special        applications. Said transgenic plants synthesizing a modified        starch are disclosed, for example, in EP 0571427, WO 95/04826,        EP 0719338, WO 96/15248, WO 96/19581, WO 96/27674, WO 97/11188,        WO 97/26362, WO 97/32985, WO 97/42328, WO 97/44472, WO 97/45545,        WO 98/27212, WO 98/40503, WO99/58688, WO 99/58690, WO 99/58654,        WO 00/08184, WO 00/08185, WO 00/08175, WO 00/28052, WO 00/77229,        WO 01/12782, WO 01/12826, WO 02/101059, WO 03/071860, WO        2004/056999, WO 2005/030942, WO 2005/030941, WO 2005/095632, WO        2005/095617, WO 2005/095619, WO 2005/095618, WO 2005/123927, WO        2006/018319, WO 2006/103107, WO 2006/108702, WO 2007/009823, WO        00/22140, WO 2006/063862, WO 2006/072603, WO 02/034923, EP        06090134.5, EP 06090228.5, EP 06090227.7, EP 07090007.1, EP        07090009.7, WO 01/14569, WO 02/79410, WO 03/33540, WO        2004/078983, WO 01/19975, WO 95/26407, WO 96/34968, WO 98/20145,        WO 99/12950, WO 99/66050, WO 99/53072, U.S. Pat. No. 6,734,341,        WO 00/11192, WO 98/22604, WO 98/32326, WO 01/98509, WO 01/98509,        WO 2005/002359, U.S. Pat. No. 5,824,790, U.S. Pat. No.        6,013,861, WO 94/04693, WO 94/09144, WO 94/11520, WO 95/35026,        WO 97/20936    -   2) transgenic plants which synthesize non starch carbohydrate        polymers or which synthesize non starch carbohydrate polymers        with altered properties in comparison to wild type plants        without genetic modification. Examples are plants producing        polyfructose, especially of the inulin and levan-type, as        disclosed in EP 0663956, WO 96/01904, WO 96/21023, WO 98/39460,        and WO 99/24593, plants producing alpha-1,4-glucans as disclosed        in WO 95/31553, US 2002031826, U.S. Pat. No. 6,284,479, U.S.        Pat. No. 5,712,107, WO 97/47806, WO 97/47807, WO 97/47808 and WO        00/14249, plants producing alpha-1,6 branched alpha-1,4-glucans,        as disclosed in WO 00/73422, plants producing alternan, as        disclosed in e.g. WO 00/47727, WO 00/73422, EP 06077301.7, U.S.        Pat. No. 5,908,975 and EP 0728213,    -   3) transgenic plants which produce hyaluronan, as for example        disclosed in WO 2006/032538, WO 2007/039314, WO 2007/039315, WO        2007/039316, JP 2006304779, and WO 2005/012529.    -   4) transgenic plants or hybrid plants, such as onions with        characteristics such as ‘high soluble solids content’, low        pungency′ (LP) and/or ‘long storage’ (LS), as described in U.S.        patent application Ser. No. 12/020,360 and 61/054,026.

Plants or plant cultivars (that can be obtained by plant biotechnologymethods such as genetic engineering) which may also be treated accordingto the invention are plants, such as cotton plants, with altered fibercharacteristics. Such plants can be obtained by genetic transformation,or by selection of plants contain a mutation imparting such alteredfiber characteristics and include:

-   -   a) Plants, such as cotton plants, containing an altered form of        cellulose synthase genes as described in WO 98/00549    -   b) Plants, such as cotton plants, containing an altered form of        rsw2 or rsw3 homologous nucleic acids as described in WO        2004/053219    -   c) Plants, such as cotton plants, with increased expression of        sucrose phosphate synthase as described in WO 01/17333    -   d) Plants, such as cotton plants, with increased expression of        sucrose synthase as described in WO 02/45485    -   e) Plants, such as cotton plants, wherein the timing of the        plasmodesmatal gating at the basis of the fiber cell is altered,        e.g. through downregulation of fiber-selective β-1,3-glucanase        as described in WO 2005/017157, or as described in EP 08075514.3        or U.S. Patent Appl. No. 61/128,938    -   f) Plants, such as cotton plants, having fibers with altered        reactivity, e.g. through the expression of        N-acetylglucosaminetransferase gene including nodC and chitin        synthase genes as described in WO 2006/136351

Plants or plant cultivars (that can be obtained by plant biotechnologymethods such as genetic engineering) which may also be treated accordingto the invention are plants, such as oilseed rape or related Brassicaplants, with altered oil profile characteristics. Such plants can beobtained by genetic transformation, or by selection of plants contain amutation imparting such altered oil profile characteristics and include:

-   -   a) Plants, such as oilseed rape plants, producing oil having a        high oleic acid content as described e.g. in U.S. Pat. Nos.        5,969,169, 5,840,946 or 6,323,392 or 6,063,947    -   b) Plants such as oilseed rape plants, producing oil having a        low linolenic acid content as described in U.S. Pat. Nos.        6,270,828, 6,169,190, or 5,965,755    -   c) Plant such as oilseed rape plants, producing oil having a low        level of saturated fatty acids as described e.g. in U.S. Pat.        No. 5,434,283 or U.S. patent application Ser. No. 12/668,303

Plants or plant cultivars (that can be obtained by plant biotechnologymethods such as genetic engineering) which may also be treated accordingto the invention are plants, such as oilseed rape or related Brassicaplants, with altered seed shattering characteristics. Such plants can beobtained by genetic transformation, or by selection of plants contain amutation imparting such altered seed shattering characteristics andinclude plants such as oilseed rape plants with delayed or reduced seedshattering as described in U.S. Patent Appl. No. 61/135,230 WO09/068313and WO10/006732.

Particularly useful transgenic plants which may be treated according tothe invention are plants containing transformation events, orcombination of transformation events, that are the subject of petitionsfor nonregulated status, in the United States of America, to the Animaland Plant Health Inspection Service (APHIS) of the United StatesDepartment of Agriculture (USDA) whether such petitions are granted orare still pending. At any time this information is readily availablefrom APHIS (4700 River Road Riverdale, Md. 20737, USA), for instance onits internet site (URLhttp://www(dot)aphis(dot)usda(dot)gov/brs/not_reg(dot)html). On thefiling date of this application the petitions for nonregulated statusthat were pending with APHIS or granted by APHIS were those whichcontains the following information:

-   -   Petition: the identification number of the petition. Technical        descriptions of the transformation events can be found in the        individual petition documents which are obtainable from APHIS,        for example on the APHIS website, by reference to this petition        number. These descriptions are herein incorporated by reference.    -   Extension of Petition: reference to a previous petition for        which an extension is requested.    -   Institution: the name of the entity submitting the petition.    -   Regulated article: the plant species concerned.    -   Transgenic phenotype: the trait conferred to the plants by the        transformation event.    -   Transformation event or line: the name of the event or events        (sometimes also designated as lines or lines) for which        nonregulated status is requested.    -   APHIS documents: various documents published by APHIS in        relation to the Petition and which can be requested with APHIS.

Additional particularly useful plants containing single transformationevents or combinations of transformation events are listed for examplein the databases from various national or regional regulatory agencies(see for example http://gmoinfo(dot)jrc(dot)it/gmp_browse(dot)aspx andhttp://www(dot)agbios(dot)com/dbase(dot)php).

Particularly useful transgenic plants which may be treated according tothe invention are plants containing transformation events, or acombination of transformation events, and that are listed for example inthe databases for various national or regional regulatory agenciesincluding Event 1143-14A (cotton, insect control, not deposited,described in WO 2006/128569); Event 1143-51B (cotton, insect control,not deposited, described in WO 2006/128570); Event 1445 (cotton,herbicide tolerance, not deposited, described in US-A 2002-120964 or WO02/034946); Event 17053 (rice, herbicide tolerance, deposited asPTA-9843, described in WO 2010/117737); Event 17314 (rice, herbicidetolerance, deposited as PTA-9844, described in WO 2010/117735); Event281-24-236 (cotton, insect control—herbicide tolerance, deposited asPTA-6233, described in WO 2005/103266 or US-A 2005-216969); Event3006-210-23 (cotton, insect control—herbicide tolerance, deposited asPTA-6233, described in US-A 2007-143876 or WO 2005/103266); Event 3272(corn, quality trait, deposited as PTA-9972, described in WO 2006/098952or US-A 2006-230473); Event 40416 (corn, insect control—herbicidetolerance, deposited as ATCC PTA-11508, described in WO 2011/075593);Event 43A47 (corn, insect control—herbicide tolerance, deposited as ATCCPTA-11509, described in WO 2011/075595); Event 5307 (corn, insectcontrol, deposited as ATCC PTA-9561, described in WO 2010/077816); EventASR-368 (bent grass, herbicide tolerance, deposited as ATCC PTA-4816,described in US-A 2006-162007 or WO 2004/053062); Event B16 (corn,herbicide tolerance, not deposited, described in US-A 2003-126634);Event BPS-CV127-9 (soybean, herbicide tolerance, deposited as NCIMB No.41603, described in WO 2010/080829); Event CE43-67B (cotton, insectcontrol, deposited as DSM ACC2724, described in US-A 2009-217423 orWO2006/128573); Event CE44-69D (cotton, insect control, not deposited,described in US-A 2010-0024077); Event CE44-69D (cotton, insect control,not deposited, described in WO 2006/128571); Event CE46-02A (cotton,insect control, not deposited, described in WO 2006/128572); EventCOT102 (cotton, insect control, not deposited, described in US-A2006-130175 or WO 2004/039986); Event COT202 (cotton, insect control,not deposited, described in US-A 2007-067868 or WO 2005/054479); EventCOT203 (cotton, insect control, not deposited, described in WO2005/054480); Event DAS40278 (corn, herbicide tolerance, deposited asATCC PTA-10244, described in WO 2011/022469); Event DAS-59122-7 (corn,insect control—herbicide tolerance, deposited as ATCC PTA 11384,described in US-A 2006-070139); Event DAS-59132 (corn, insectcontrol—herbicide tolerance, not deposited, described in WO2009/100188); Event DAS68416 (soybean, herbicide tolerance, deposited asATCC PTA-10442, described in WO 2011/066384 or WO 2011/066360); EventDP-098140-6 (corn, herbicide tolerance, deposited as ATCC PTA-8296,described in US-A 2009-137395 or WO 2008/112019); Event DP-305423-1(soybean, quality trait, not deposited, described in US-A 2008-312082 orWO 2008/054747); Event DP-32138-1 (corn, hybridization system, depositedas ATCC PTA-9158, described in US-A 2009-0210970 or WO 2009/103049);Event DP-356043-5 (soybean, herbicide tolerance, deposited as ATCCPTA-8287, described in US-A 2010-0184079 or WO 2008/002872); Event EE-1(brinjal, insect control, not deposited, described in WO 2007/091277);Event FI117 (corn, herbicide tolerance, deposited as ATCC 209031,described in US-A 2006-059581 or WO 98/044140); Event GA21 (corn,herbicide tolerance, deposited as ATCC 209033, described in US-A2005-086719 or WO 98/044140); Event GG25 (corn, herbicide tolerance,deposited as ATCC 209032, described in US-A 2005-188434 or WO98/044140); Event GHB119 (cotton, insect control—herbicide tolerance,deposited as ATCC PTA-8398, described in WO 2008/151780); Event GHB614(cotton, herbicide tolerance, deposited as ATCC PTA-6878, described inUS-A 2010-050282 or WO 2007/017186); Event GJ11 (corn, herbicidetolerance, deposited as ATCC 209030, described in US-A 2005-188434 or WO98/044140); Event GM RZ13 (sugar beet, virus resistance, deposited asNCIMB-41601, described in WO 2010/076212); Event H7-1 (sugar beet,herbicide tolerance, deposited as NCIMB 41158 or NCIMB 41159, describedin US-A 2004-172669 or WO 2004/074492); Event JOPLIN1 (wheat, diseasetolerance, not deposited, described in US-A 2008-064032); Event LL27(soybean, herbicide tolerance, deposited as NCIMB41658, described in WO2006/108674 or US-A 2008-320616); Event LL55 (soybean, herbicidetolerance, deposited as NCIMB 41660, described in WO 2006/108675 or US-A2008-196127); Event LLcotton25 (cotton, herbicide tolerance, depositedas ATCC PTA-3343, described in WO 03/013224 or US-A 2003-097687); EventLLRICE06 (rice, herbicide tolerance, deposited as ATCC-23352, describedin U.S. Pat. No. 6,468,747 or WO 00/026345); Event LLRICE601 (rice,herbicide tolerance, deposited as ATCC PTA-2600, described in US-A2008-2289060 or WO 00/026356); Event LY038 (corn, quality trait,deposited as ATCC PTA-5623, described in US-A 2007-028322 or WO2005/061720); Event MIR162 (corn, insect control, deposited as PTA-8166,described in US-A 2009-300784 or WO 2007/142840); Event MIR604 (corn,insect control, not deposited, described in US-A 2008-167456 or WO2005/103301); Event MON15985 (cotton, insect control, deposited as ATCCPTA-2516, described in US-A 2004-250317 or WO 02/100163); Event MON810(corn, insect control, not deposited, described in US-A 2002-102582);Event MON863 (corn, insect control, deposited as ATCC PTA-2605,described in WO 2004/011601 or US-A 2006-095986); Event MON87427 (corn,pollination control, deposited as ATCC PTA-7899, described in WO2011/062904); Event MON87460 (corn, stress tolerance, deposited as ATCCPTA-8910, described in WO 2009/111263 or US-A 2011-0138504); EventMON87701 (soybean, insect control, deposited as ATCC PTA-8194, describedin US-A 2009-130071 or WO 2009/064652); Event MON87705 (soybean, qualitytrait—herbicide tolerance, deposited as ATCC PTA-9241, described in US-A2010-0080887 or WO 2010/037016); Event MON87708 (soybean, herbicidetolerance, deposited as ATCC PTA9670, described in WO 2011/034704);Event MON87754 (soybean, quality trait, deposited as ATCC PTA-9385,described in WO 2010/024976); Event MON87769 (soybean, quality trait,deposited as ATCC PTA-8911, described in US-A 2011-0067141 or WO2009/102873); Event MON88017 (corn, insect control—herbicide tolerance,deposited as ATCC PTA-5582, described in US-A 2008-028482 or WO2005/059103); Event MON88913 (cotton, herbicide tolerance, deposited asATCC PTA-4854, described in WO 2004/072235 or US-A 2006-059590); EventMON89034 (corn, insect control, deposited as ATCC PTA-7455, described inWO 2007/140256 or US-A 2008-260932); Event MON89788 (soybean, herbicidetolerance, deposited as ATCC PTA-6708, described in US-A 2006-282915 orWO 2006/130436); Event MS11 (oilseed rape, pollination control—herbicidetolerance, deposited as ATCC PTA-850 or PTA-2485, described in WO01/031042); Event MS8 (oilseed rape, pollination control—herbicidetolerance, deposited as ATCC PTA-730, described in WO 01/041558 or US-A2003-188347); Event NK603 (corn, herbicide tolerance, deposited as ATCCPTA-2478, described in US-A 2007-292854); Event PE-7 (rice, insectcontrol, not deposited, described in WO 2008/114282); Event RF3 (oilseedrape, pollination control—herbicide tolerance, deposited as ATCC PTA730,described in WO 01/041558 or US-A 2003-188347); Event RT73 (oilseedrape, herbicide tolerance, not deposited, described in WO 02/036831 orUS-A 2008-070260); Event T227-1 (sugar beet, herbicide tolerance, notdeposited, described in WO 02/44407 or US-A 2009-265817); Event T25(corn, herbicide tolerance, not deposited, described in US-A 2001-029014or WO 01/051654); Event T304-40 (cotton, insect control—herbicidetolerance, deposited as ATCC PTA-8171, described in US-A 2010-077501 orWO 2008/122406); Event T342-142 (cotton, insect control, not deposited,described in WO 2006/128568); Event TC1507 (corn, insectcontrol—herbicide tolerance, not deposited, described in US-A2005-039226 or WO 2004/099447); Event VIP1034 (corn, insectcontrol—herbicide tolerance, deposited as ATCC PTA-3925, described in WO03/052073), Event 32316 (corn, insect control-herbicide tolerance,deposited as PTA11507, described in WO 2011/084632), Event 4114 (corn,insect control-herbicide tolerance, deposited as PTA-11506, described inWO 2011/084621).

In the context of the present invention, the active compoundcombinations or compositions according to the invention are applied ontheir own or in a suitable formulation to the seed. Preferably, the seedis treated in a state in which it is sufficiently stable so that thetreatment does not cause any damage. In general, treatment of the seedmay take place at any point in time between harvesting and sowing.Usually, the seed used is separated from the plant and freed from cobs,shells, stalks, coats, hairs or the flesh of the fruits. Thus, it ispossible to use, for example, seed which has been harvested, cleaned anddried to a moisture content of less than 15% by weight. Alternatively,it is also possible to use seed which, after drying, has been treated,for example, with water and then dried again.

When treating the seed, care must generally be taken that the amount ofthe composition according to the invention applied to the seed and/orthe amount of further additives is chosen in such a way that thegermination of the seed is not adversely affected, or that the resultingplant is not damaged. This must be borne in mind in particular in thecase of active compounds which may have phytotoxic effects at certainapplication rates.

The compositions according to the invention can be applied directly,that is to say without comprising further components and without havingbeen diluted. In general, it is preferable to apply the compositions tothe seed in the form of a suitable formulation. Suitable formulationsand methods for the treatment of seed are known to the person skilled inthe art and are described, for example, in the following documents: U.S.Pat. Nos. 4,272,417 A, 4,245,432 A, 4,808,430 A, 5,876,739 A, US2003/0176428 A1, WO 2002/080675 A1, WO 2002/028186 A2.

The active compound combinations which can be used according to theinvention can be converted into customary seed dressing formulations,such as solutions, emulsions, suspensions, powders, foams, slurries orother coating materials for seed, and also ULV formulations.

These formulations are prepared in a known manner by mixing the activecompounds or active compound combinations with customary additives, suchas, for example, customary extenders and also solvents or diluents,colorants, wetting agents, dispersants, emulsifiers, defoamers,preservatives, secondary thickeners, adhesives, gibberellins and wateras well.

Suitable colorants that may be present in the seed dressing formulationswhich can be used according to the invention include all colorantscustomary for such purposes. Use may be made both of pigments, ofsparing solubility in water, and of dyes, which are soluble in water.Examples that may be mentioned include the colorants known under thedesignations Rhodamine B, C.I. Pigment Red 112, and C.I. Solvent Red 1.Suitable wetting agents that may be present in the seed dressingformulations which can be used according to the invention include allsubstances which promote wetting and are customary in the formulation ofactive agrochemical substances. With preference it is possible to usealkylnaphthalene-sulfonates, such as diisopropyl- ordiisobutylnaphthalene-sulfonates.

Suitable dispersants and/or emulsifiers that may be present in the seeddressing formulations which can be used according to the inventioninclude all nonionic, anionic, and cationic dispersants which arecustomary in the formulation of active agrochemical substances. Withpreference, it is possible to use nonionic or anionic dispersants ormixtures of nonionic or anionic dispersants. Particularly suitablenonionic dispersants are ethylene oxide-propylene oxide block polymers,alkylphenol polyglycol ethers, and tristyrylphenol polyglycol ethers,and their phosphated or sulfated derivatives. Particularly suitableanionic dispersants are lignosulfonates, polyacrylic salts, andarylsulfonate-formaldehyde condensates.

Defoamers that may be present in the seed dressing formulations to beused according to the invention include all foam-inhibiting compoundswhich are customary in the formulation of agrochemically activecompounds. Preference is given to using silicone defoamers, magnesiumstearate, silicone emulsions, long-chain alcohols, fatty acids and theirsalts and also organofluorine compounds and mixtures thereof.

Preservatives that may be present in the seed dressing formulations tobe used according to the invention include all compounds which can beused for such purposes in agrochemical compositions. By way of example,mention may be made of dichlorophen and benzyl alcohol hemiformal.

Secondary thickeners that may be present in the seed dressingformulations to be used according to the invention include all compoundswhich can be used for such purposes in agrochemical compositions.Preference is given to cellulose derivatives, acrylic acid derivatives,polysaccharides, such as xanthan gum or Veegum, modified clays,phyllosilicates, such as attapulgite and bentonite, and also finelydivided silicic acids. Suitable adhesives that may be present in theseed dressing formulations to be used according to the invention includeall customary binders which can be used in seed dressings.Polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylosemay be mentioned as being preferred.

Suitable gibberellins that may be present in the seed dressingformulations to be used according to the invention are preferably thegibberellins A1, A3 (=gibberellic acid), A4 and A7; particularpreference is given to using gibberellic acid. The gibberellins areknown (cf. R. Wegler “Chemie der Pflanzenschutz- andSchädlingsbekampfungsmittel” [Chemistry of Crop Protection Agents andPesticides], Vol. 2, Springer Verlag, 1970, pp. 401-412).

The seed dressing formulations which can be used according to theinvention may be used directly or after dilution with water beforehandto treat seed of any of a very wide variety of types. The seed dressingformulations which can be used according to the invention or theirdilute preparations may also be used to dress seed of transgenic plants.In this context, synergistic effects may also arise in interaction withthe substances formed by expression.

Suitable mixing equipment for treating seed with the seed dressingformulations which can be used according to the invention or thepreparations prepared from them by adding water includes all mixingequipment which can commonly be used for dressing. The specificprocedure adopted when dressing comprises introducing the seed into amixer, adding the particular desired amount of seed dressingformulation, either as it is or following dilution with waterbeforehand, and carrying out mixing until the formulation is uniformlydistributed on the seed. Optionally, a drying operation follows.

The active compounds or compositions according to the invention havestrong microbicidal activity and can be used for controlling unwantedmicroorganisms, such as fungi and bacteria, in crop protection andmaterial protection.

In crop protection, fungicides can be used for controllingPlasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes,Ascomycetes, Basidiomycetes and Deuteromycetes.

In crop protection, bactericides can be used for controllingPseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceaeand Streptomycetaceae.

The fungicidal compositions according to the invention can be used forthe curative or protective control of phytopathogenic fungi.Accordingly, the invention also relates to curative and protectivemethods for controlling phytopathogenic fungi using the active compoundcombinations or compositions according to the invention, which areapplied to the seed, the plant or plant parts, the fruit or the soil inwhich the plants grow. Preference is given to application onto the plantor the plant parts, the fruits or the soil in which the plants grow.

The compositions according to the invention for combatingphytopathogenic fungi in crop protection comprise an active, butnon-phytotoxic amount of the compounds according to the invention.“Active, but non-phytotoxic amount” shall mean an amount of thecomposition according to the invention which is sufficient to control orto completely kill the plant disease caused by fungi, which amount atthe same time does not exhibit noteworthy symptoms of phytotoxicity.These application rates generally may be varied in a broader range,which rate depends on several factors, e.g. the phytopathogenic fungi,the plant or crop, the climatic conditions and the ingredients of thecomposition according to the invention.

The fact that the active compounds, at the concentrations required forthe controlling of plant diseases, are well tolerated by plants permitsthe treatment of aerial plant parts, of vegetative propagation materialand seed, and of the soil.

According to the invention, it is possible to treat all plants and partsof plants. Plants are to be understood here as meaning all plants andplant populations, such as wanted and unwanted wild plants or cropplants (including naturally occurring crop plants). Crop plants can beplants which can be obtained by conventional breeding and optimizationmethods or by biotechnological and genetic engineering methods orcombinations of these methods, including the transgenic plants andincluding plant cultivars which can or cannot be protected by plantvariety protection rights. Parts of plants are to be understood asmeaning all above-ground and below-ground parts and organs of theplants, such as shoot, leaf, flower and root, examples which may bementioned being leaves, needles, stems, trunks, flowers, fruit bodies,fruits and seeds and also roots, tubers and rhizomes. Plant parts alsoinclude harvested material and vegetative and generative propagationmaterial, for example seedlings, tubers, rhizomes, cuttings and seeds.Preference is given to the treatment of the plants and the above-groundand below-ground parts and organs of the plants, such as shoot, leaf,flower and root, examples which may be mentioned being leaves, needles,stems, trunks, flowers, and fruits.

The active compounds of the invention, in combination with good planttolerance and favourable toxicity to warm-blooded animals and beingtolerated well by the environment, are suitable for protecting plantsand plant organs, for increasing the harvest yields, for improving thequality of the harvested material. They may be preferably employed ascrop protection agents. They are active against normally sensitive andresistant species and against all or some stages of development.

The following plants may be mentioned as plants which can be treatedaccording to the invention: cotton, flax, grapevines, fruit, vegetable,such as Rosaceae sp. (for example pomaceous fruit, such as apples andpears, but also stone fruit, such as apricots, cherries, almonds andpeaches and soft fruit such as strawberries), Ribesioidae sp.,Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp.,Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceaesp. (for example banana trees and plantations), Rubiaceae sp. (forexample coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (forexample lemons, oranges and grapefruit), Solanaceae sp. (for exampletomatoes), Liliaceae sp., Asteraceae sp. (for example lettuce),Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp.(for example cucumbers), Alliaceae sp. (for example leek, onions),Papilionaceae sp. (for example peas); major crop plants, such Gramineaesp. (for example maize, lawn, cereals such as wheat, rye, rice, barley,oats, millet and triticale), Asteraceae sp. (for example sunflowers),Brassicaceae sp. (for example white cabbage, red cabbage, broccoli,cauliflowers, Brussels sprouts, pak choi, kohlrabi, garden radish, andalso oilseed rape, mustard, horseradish and cress), Fabacae sp. (forexample beans, peas, peanuts), Papilionaceae sp. (for example soyabeans), Solanaceae sp. (for example potatoes), Chenopodiaceae sp. (forexample sugar beet, fodder beet, Swiss chard, beetroot); crop plants andornamental plants in garden and forest; and also in each casegenetically modified varieties of these plants.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andparts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineeringmethods, if appropriate in combination with conventional methods(genetically modified organisms), and parts thereof are treated. Theterms “parts”, “parts of plants” and “plant parts” have been explainedabove. Particularly preferably, plants of the plant cultivars which arein each case commercially available or in use are treated according tothe invention. Plant cultivars are to be understood as meaning plantshaving novel properties (“traits”) which have been obtained byconventional breeding, by mutagenesis or by recombinant DNA techniques.These can be cultivars, bio- or genotypes.

In material protection the substances of the invention may be used forthe protection of technical materials against infestation anddestruction by undesirable fungi and/or microorganisms.

Technical materials are understood to be in the present contextnon-living materials that have been prepared for use in engineering. Forexample, technical materials that are to be protected againstmicrobiological change or destruction by the active materials of theinvention can be adhesives, glues, paper and cardboard, textiles,carpets, leather, wood, paint and plastic articles, cooling lubricantsand other materials that can be infested or destroyed bymicro-organisms. Within the context of materials to be protected arealso parts of production plants and buildings, for example coolingcircuits, cooling and heating systems, air conditioning and ventilationsystems, which can be adversely affected by the propagation of fungiand/or microorganisms. Within the context of the present invention,preferably mentioned as technical materials are adhesives, glues, paperand cardboard, leather, wood, paints, cooling lubricants and heatexchanger liquids, particularly preferred is wood. The combinationsaccording to the invention can prevent disadvantageous effects likedecaying, dis- and decoloring, or molding. The active compoundcombinations and compositions according to the invention can likewise beemployed for protecting against colonization of objects, in particularship hulls, sieves, nets, buildings, quays and signalling installations,which are in contact with sea water or brackish water.

The method of treatment according to the invention can also be used inthe field of protecting storage goods against attack of fungi andmicroorganisms. According to the present invention, the term “storagegoods” is understood to denote natural substances of vegetable or animalorigin and their processed forms, which have been taken from the naturallife cycle and for which long-term protection is desired. Storage goodsof vegetable origin, such as plants or parts thereof, for examplestalks, leafs, tubers, seeds, fruits or grains, can be protected in thefreshly harvested state or in processed form, such as pre-dried,moistened, comminuted, ground, pressed or roasted. Also falling underthe definition of storage goods is timber, whether in the form of crudetimber, such as construction timber, electricity pylons and barriers, orin the form of finished articles, such as furniture or objects made fromwood. Storage goods of animal origin are hides, leather, furs, hairs andthe like. The combinations according the present invention can preventdisadvantageous effects such as decay, discoloration or mold. Preferably“storage goods” is understood to denote natural substances of vegetableorigin and their processed forms, more preferably fruits and theirprocessed forms, such as pomes, stone fruits, soft fruits and citrusfruits and their processed forms.

Some pathogens of fungal diseases which can be treated according to theinvention may be mentioned by way of example, but not by way oflimitation:

Diseases caused by powdery mildew pathogens, such as, for example,Blumeria species, such as, for example, Blumeria graminis; Podosphaeraspecies, such as, for example, Podosphaera leucotricha; Sphaerothecaspecies, such as, for example, Sphaerotheca fuliginea; Uncinula species,such as, for example, Uncinula necator;

Diseases caused by rust disease pathogens, such as, for example,Gymnosporangium species, such as, for example, Gymnosporangium sabinae;Hemileia species, such as, for example, Hemileia vastatrix; Phakopsoraspecies, such as, for example, Phakopsora pachyrhizi and Phakopsorameibomiae; Puccinia species, such as, for example, Puccinia recondita orPuccinia triticina; Uromyces species, such as, for example, Uromycesappendiculatus;

Diseases caused by pathogens from the group of the Oomycetes, such as,for example, Bremia species, such as, for example, Bremia lactucae;Peronospora species, such as, for example, Peronospora pisi or P.brassicae; Phytophthora species, such as, for example Phytophthorainfestans; Plasmopara species, such as, for example, Plasmoparaviticola; Pseudoperonospora species, such as, for example,Pseudoperonospora humuli or Pseudoperonospora cubensis; Pythium species,such as, for example, Pythium ultimum; Leaf blotch diseases and leafwilt diseases caused, for example, by Alternaria species, such as, forexample, Alternaria solani; Cercospora species, such as, for example,Cercospora beticola; Cladiosporium species, such as, for example,Cladiosporium cucumerinum; Cochliobolus species, such as, for example,Cochliobolus sativus (conidia form: Drechslera, Syn: Helminthosporium);Colletotrichum species, such as, for example, Colletotrichumlindemuthanium; Cycloconium species, such as, for example, Cycloconiumoleaginum; Diaporthe species, such as, for example, Diaporthe citri;Elsinoe species, such as, for example, Elsinoe fawcettii; Gloeosporiumspecies, such as, for example, Gloeosporium laeticolor; Glomerellaspecies, such as, for example, Glomerella cingulata; Guignardia species,such as, for example, Guignardia bidwelli; Leptosphaeria species, suchas, for example, Leptosphaeria maculans; Magnaporthe species, such as,for example, Magnaporthe grisea; Microdochium species, such as, forexample, Microdochium nivale; Mycosphaerella species, such as, forexample, Mycosphaerella graminicola and M. fijiensis; Phaeosphaeriaspecies, such as, for example, Phaeosphaeria nodorum; Pyrenophoraspecies, such as, for example, Pyrenophora teres; Ramularia species,such as, for example, Ramularia collo-cygni; Rhynchosporium species,such as, for example, Rhynchosporium secalis; Septoria species, such as,for example, Septoria apii; Typhula species, such as, for example,Typhula incarnata; Venturia species, such as, for example, Venturiainaequalis;

Root and stem diseases caused, for example, by Corticium species, suchas, for example, Corticium graminearum; Fusarium species, such as, forexample, Fusarium oxysporum; Gaeumannomyces species, such as, forexample, Gaeumannomyces graminis; Rhizoctonia species, such as, forexample Rhizoctonia solani; Tapesia species, such as, for example,Tapesia acuformis; Thielaviopsis species, such as, for example,Thielaviopsis basicola;

Ear and panicle diseases (including maize cobs) caused, for example, byAlternaria species, such as, for example, Alternaria spp.; Aspergillusspecies, such as, for example, Aspergillus flavus; Cladosporium species,such as, for example, Cladosporium cladosporioides; Claviceps species,such as, for example, Claviceps purpurea; Fusarium species, such as, forexample, Fusarium culmorum; Gibberella species, such as, for example,Gibberella zeae; Monographella species, such as, for example,Monographella nivalis; Septoria species, such as for example, Septorianodorum;

Diseases caused by smut fungi, such as, for example, Sphacelothecaspecies, such as, for example, Sphacelotheca reiliana; Tilletia species,such as, for example, Tilletia caries; T. controversa; Urocystisspecies, such as, for example, Urocystis occulta; Ustilago species, suchas, for example, Ustilago nuda; U. nuda tritici;

Fruit rot caused, for example, by Aspergillus species, such as, forexample, Aspergillus flavus; Botrytis species, such as, for example,Botrytis cinerea; Penicillium species, such as, for example, Penicilliumexpansum and P. purpurogenum; Sclerotinia species, such as, for example,Sclerotinia sclerotiorum; Verticilium species, such as, for example,Verticilium alboatrum;

Seed- and soil-borne rot and wilt diseases, and also diseases ofseedlings, caused, for example, by Fusarium species, such as, forexample, Fusarium culmorum; Phytophthora species, such as, for example,Phytophthora cactorum; Pythium species, such as, for example, Pythiumultimum; Rhizoctonia species, such as, for example, Rhizoctonia solani;Sclerotium species, such as, for example, Sclerotium rolfsii;

Cancerous diseases, galls and witches' broom caused, for example, byNectria species, such as, for example, Nectria galligena;

Wilt diseases caused, for example, by Monilinia species, such as, forexample, Monilinia laxa; Deformations of leaves, flowers and fruitscaused, for example, by Taphrina species, such as, for example, Taphrinadeformans;

Degenerative diseases of woody plants caused, for example, by Escaspecies, such as, for example, Phaemoniella clamydospora andPhaeoacremonium aleophilum and Fomitiporia mediterranea;

Diseases of flowers and seeds caused, for example, by Botrytis species,such as, for example, Botrytis cinerea;

Diseases of plant tubers caused, for example, by Rhizoctonia species,such as, for example, Rhizoctonia solani; Helminthosporium species, suchas, for example, Helminthosporium solani;

Diseases caused by bacteriopathogens, such as, for example, Xanthomonasspecies, such as, for example, Xanthomonas campestris pv. oryzae;Pseudomonas species, such as, for example, Pseudomonas syringae pv.lachrymans; Erwinia species, such as, for example, Erwinia amylovora.

Preference is given to controlling the following diseases of soya beans:

Fungal diseases on leaves, stems, pods and seeds caused, for example, byalternaria leaf spot (Alternaria spec. atrans tenuissima), anthracnose(Colletotrichum gloeosporoides dematium var. truncatum), brown spot(Septoria glycines), cercospora leaf spot and blight (Cercosporakikuchii), choanephora leaf blight (Choanephora infundibulifera trispora(Syn.)), dactuliophora leaf spot (Dactuliophora glycines), downy mildew(Peronospora manshurica), drechslera blight (Drechslera glycini),frogeye leaf spot (Cercospora sojina), leptosphaerulina leaf spot(Leptosphaerulina trifolii), phyllostica leaf spot (Phyllostictasojaecola), pod and stem blight (Phomopsis sojae), powdery mildew(Microsphaera diffusa), pyrenochaeta leaf spot (Pyrenochaeta glycines),rhizoctonia aerial, foliage, and web blight (Rhizoctonia solani), rust(Phakopsora pachyrhizi Phakopsora meibomiae), scab (Sphacelomaglycines), stemphylium leaf blight (Stemphylium botryosum), target spot(Corynespora cassiicola).

Fungal diseases on roots and the stem base caused, for example, by blackroot rot (Calonectria crotalariae), charcoal rot (Macrophominaphaseolina), fusarium blight or wilt, root rot, and pod and collar rot(Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusariumequiseti), mycoleptodiscus root rot (Mycoleptodiscus terrestris),neocosmospora (Neocosmopspora vasinfecta), pod and stem blight(Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var.caulivora), phytophthora rot (Phytophthora megasperma), brown stem rot(Phialophora gregata), pythium rot (Pythium aphanidermatum, Pythiumirregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum),rhizoctonia root rot, stem decay, and damping-off (Rhizoctonia solani),sclerotinia stem decay (Sclerotinia sclerotiorum), sclerotinia Southernblight (Sclerotinia rolfsii), thielaviopsis root rot (Thielaviopsisbasicola).

It is also possible to control resistant strains of the organismsmentioned above.

Microorganisms capable of degrading or changing the industrial materialswhich may be mentioned are, for example, bacteria, fungi, yeasts, algaeand slime organisms. The active compounds according to the inventionpreferably act against fungi, in particular moulds, wood-discolouringand wood-destroying fungi (Basidiomycetes) and against slime organismsand algae. Microorganisms of the following genera may be mentioned asexamples: Alternaria, such as Alternaria tenuis, Aspergillus, such asAspergillus niger, Chaetomium, such as Chaetomium globosum, Coniophora,such as Coniophora puetana, Lentinus, such as Lentinus tigrinus,Penicillium, such as Penicillium glaucum, Polyporus, such as Polyporusversicolor, Aureobasidium, such as Aureobasidium pullulans, Sclerophoma,such as Sclerophoma pityophila, Trichoderma, such as Trichoderma viride,Escherichia, such as Escherichia coli, Pseudomonas, such as Pseudomonasaeruginosa, and Staphylococcus, such as Staphylococcus aureus.

In addition, the compounds of the formula (I) according to the inventionalso have very good antimycotic activity. They have a very broadantimycotic activity spectrum in particular against dermatophytes andyeasts, moulds and diphasic fungi (for example against Candida speciessuch as Candida albicans, Candida glabrata) and Epidermophytonfloccosum, Aspergillus species such as Aspergillus niger and Aspergillusfumigatus, Trichophyton species such as Trichophyton mentagrophytes,Microsporon species such as Microsporon canis and audouinii. The list ofthese fungi by no means limits the mycotic spectrum which can becovered, but is only for illustration.

When applying the compounds according to the invention the applicationrates can be varied within a broad range. The dose of activecompound/application rate usually applied in the method of treatmentaccording to the invention is generally and advantageously

-   -   for treatment of part of plants, e.g. leafs (foliar treatment):        from 0.1 to 10,000 g/ha, preferably from 10 to 1,000 g/ha, more        preferably from 50 to 300 g/ha; in case of drench or drip        application, the dose can even be reduced, especially while        using inert substrates like rockwool or perlite;    -   for seed treatment: from 2 to 200 g per 100 kg of seed,        preferably from 3 to 150 g per 100 kg of seed, more preferably        from 2.5 to 25 g per 100 kg of seed, even more preferably from        2.5 to 12.5 g per 100 kg of seed;    -   for soil treatment: from 0.1 to 10,000 g/ha, preferably from 1        to 5,000 g/ha.

The doses herein indicated are given as illustrative examples of themethod according to the invention. A person skilled in the art will knowhow to adapt the application doses, notably according to the nature ofthe plant or crop to be treated.

The combination according to the invention can be used in order toprotect plants within a certain time range after the treatment againstpests and/or phytopathogenic fungi and/or microorganisms. The timerange, in which protection is effected, spans in general 1 to 28 days,preferably 1 to 14 days, more preferably 1 to 10 days, even morepreferably 1 to 7 days after the treatment of the plants with thecombinations or up to 200 days after the treatment of plant propagationmaterial.

Furthermore combinations and compositions according to the invention mayalso be used to reduce the contents of mycotoxins in plants and theharvested plant material and therefore in foods and animal feed stuffmade therefrom. Especially but not exclusively the following mycotoxinscan be specified: Deoxynivalenole (DON), Nivalenole, 15-Ac-DON,3-Ac-DON, T2-und HT2-Toxins, Fumonisines, Zearalenone Moniliformine,Fusarine, Diaceotoxyscirpenole (DAS), Beauvericine, Enniatine,Fusaroproliferine, Fusarenole, Ochratoxines, Patuline, Ergotalkaloidesund Aflatoxines, which are caused for example by the following fungaldiseases: Fusarium spec., like Fusarium acuminatum, F. avenaceum, F.crookwellense, F. culmorum, F. graminearum (Gibberella zeae), F.equiseti, F. fujikoroi, F. musarum, F. oxysporum, F. proliferatum, F.poae, F. pseudograminearum, F. sambucinum, F. scirpi, F. semitectum, F.solani, F. sporotrichoides, F. langsethiae, F. subglutinans, F.tricinctum, F. verticiffioides and others but also by Aspergillus spec.,Penicillium spec., Claviceps purpurea, Stachybotrys spec. and others.

The present invention further relates to a composition as herein-definedcomprising at least one further active ingredient selected from thegroup of the insecticides, attractants, sterilants, bactericides,acaricides, nematicides, fungicides, growth regulators, herbicides,fertilizers, safeners and semiochemicals.

The present invention further relates to a method for controllingphytopathogenic harmful fungi, characterized in that an active compoundcombination as herein-defined is applied to the phytopathogenic harmfulfungi and/or their habitat.

The present invention further relates to a process for producingcompositions for controlling phytopathogenic harmful fungi,characterized in that an active compound combination as herein-definedis mixed with extenders and/or surfactants.

The present invention further relates to the use of an active compoundcombination as herein-defined for control of phytopathogenic harmfulfungi.

The present invention further relates to the use of an active compoundcombination as herein-defined for the treatment of transgenic plants.

The present invention further relates to the use of an active compoundcombination as herein-defined for the treatment of seed and of seed oftransgenic plants.

N-cyclopropyl amides of formula (I) wherein T represents an oxygen atom,can be prepared by condensation of a substituted N-cyclopropylbenzylamine with3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carbonyl chlorideaccording to WO-2007/087906 (process P1) and WO-2010/130767 (process P1step 10).

Substituted N-cyclopropyl benzylamines are known or can be prepared byknown processes such as the reductive amination of a substitutedaldehyde with cyclopropanamine (J. Med. Chem., 2012, 55 (1), 169-196) orby nucleophilic substitution of a substituted benzyl alkyl (oraryl)sulfonate or a substituted benzyl halide with cyclopropanamine(Bioorg. Med. Chem., 2006, 14, 8506-8518 and WO-2009/140769).

3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carbonyl chloride canbe prepared according to WO2010/130767 (process P1—steps 9 or 11)

N-cyclopropyl thioamides of formula (I) wherein T represents a sulfuratom, can be prepared by thionation of a N-cyclopropyl amide of formula(I) wherein T represents a oxygen atom, according to WO-2009/016220(process P1) and WO-2010/130767 (process P3).

The following examples illustrate in a non limiting manner thepreparation of the compounds of formula (I) according to the invention.

Preparation ofN-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide(compound A1) Step A: preparation ofN-(2-isopropylbenzyl)cyclopropanamine

To a solution of 55.5 g (971 mmol) of cyclopropanamine in 900 mL ofmethanol, are successively added 20 g of 3 Å molecular sieves and 73 g(1.21 mol) of acetic acid. 72 g (486 mmol) of 2-isopropylbenzaldehydeare then added dropwise and the reaction mixture is further heated atreflux for 4 hours.

The reaction mixture is then cooled to 0° C. and 45.8 g (729 mmol) ofsodium cyanoborohydride are added by portion in 10 min and the reactionmixture is stirred again for 3 hours at reflux. The cooled reactionmixture is filtered over a cake of diatomaceous earth. The cake iswashed abundantly by methanol and the methanolic extracts areconcentrated under vacuum. Water is then added to the residue and the pHis adjusted to 12 with 400 mL of a 1 N aqueous solution of sodiumhydroxide. The watery layer is extracted with ethyl acetate, washed bywater (2×300 mL) and dried over magnesium sulfate to yield 81.6 g (88%)of N-(2-isopropylbenzyl)cyclopropanamine as a yellow oil used as such inthe next step.

The hydrochloride salt can be prepared by dissolvingN-(2-isopropylbenzyl)cyclopropanamine in diethylether (1.4 mL/g) at 0°C. followed by addition of a 2 M solution of hydrochloric acid indiethylether (1.05 eq.). After a 2 hours stirring,N-(2-isopropylbenzyl)cyclopropanamine hydrochloride (1:1) is filteredoff, washed by diethylether and dried under vacuum at 40° C. for 48hours. Mp (melting point)=149° C.

Step B: preparation ofN-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide

To 40.8 g (192 mmol) of N-(2-isopropylbenzyl)cyclopropanamine in 1 L ofdry tetrahydrofurane are added at room temperature, 51 mL (366 mmol) oftriethylamine. A solution of 39.4 g (174 mmol) of3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carbonyl chloride in800 mL of dry tetrahydrofurane is then added dropwise while maintainingthe temperature below 34° C. The reaction mixture is heated at refluxfor 2 hours then left overnight at room temperature. Salts are filteredoff and the filtrate is concentrated under vacuum to yield 78.7 g of abrown oil. Column chromatography on silica gel (750 g—gradientn-heptane/ethyl acetate) yields 53 g (71% yield) ofN-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamideas a yellow oil that slowly crystallizes. Mp=76-79° C.

In the same way, compounds A2 to A19 can be prepared according to thepreparation described for compound A1.

Preparation ofN-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamide(compound A20)

A solution of 14.6 g (65 mmol) of phosphorus pentasulfide and 48 g (131mmol) ofN-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamidein 500 ml of dioxane are heated at 100° C. for 2 hours. 50 ml of waterare then added and the reaction mixture is further heated at 100° C. foranother hour. The cooled reaction mixture is filtered over a basicalumina cartridge. The cartridge is washed by dichloromethane and thecombined organic extracts are dried over magnesium sulfate andconcentrated under vacuum to yield 55.3 g of an orange oil. The residueis tritured with a few mL of diethylether until crystallisation occurs.Crystals are filtered off and dried under vacuum at 40° C. for 15 hoursto yield 46.8 g (88% yield) ofN-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamide.Mp=64-70° C.

Table 1 provides the log P and NMR data (′H) of compounds A1 to A20.

In table 1, the log P values were determined in accordance with EECDirective 79/831 Annex V.A8 by HPLC (High Performance LiquidChromatography) on a reversed-phase column (C 18), using the methoddescribed below:

Temperature: 40° C.; Mobile phases: 0.1% aqueous formic acid andacetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile.

Calibration was carried out using unbranched alkan-2-ones (comprising 3to 16 carbon atoms) with known log P values (determination of the log Pvalues by the retention times using linear interpolation between twosuccessive alkanones). lambda-max-values were determined usingUV-spectra from 200 nm to 400 nm and the peak values of thechromatographic signals.

Cmpd logP NMR A1 3.35 ¹H NMR (500 MHz, CHCl₃-d): ppm 0.64 (bs, 4H), 1.21(d, J = 6.60 Hz, 6H), 2.44-2.80 (m, 1H), 3.01-3.29 (m, 1H), 3.78 (s,3H), 4.76 (bs, 2H), 6.89 (t, J = 54.70 Hz, 1H), 7.12-7.33 (m, 4H). A23.44 ¹H NMR (500 MHz, CHCl₃-d): ppm 0.47-0.77 (m, 6H), 0.80-1.04 (m,2H), 1.92 (bs, 1H), 2.66 (bs, 1H), 3.80 (s, 3H), 4.92 (bs, 2H), 6.90 (t,J = 54.50 Hz, 1H), 7.01-7.25 (m, 4H). A3 4.06 ¹H NMR (500 MHz, CHCl₃-d):ppm 0.61 (bs, 4H), 1.46 (s, 9H), 2.77-2.98 (m, 1H), 3.89 (s, 3H), 5.05(bs, 2 H), 6.91 (t, J = 54.70 Hz, 1H), 7.20 (bs, 3H), 7.35-7.48 (m, 1H).A4 3.76 ¹H NMR (300 MHz, CHCl₃-d): ppm 0.65-0.69 (m, 4H), 1.21 (t, 3H),2.62-2.64 (m, 3H), 3.81 (s, 3H), 4.70 (s, 2H), 6.85 (t, J = 54.6 Hz,1H), 7.04-7.22 (m, 3H). A5 4.09 ¹H NMR (500 MHz, CHCl₃-d): ppm 0.63-0.73(m, 4H), 1.22 (d, J = 6.92 Hz, 6H), 2.59-2.87 (m, 1H), 2.98-3.30 (m,1H), 3.82 (s, 3H), 4.74 (bs, 2H), 6.88 (t, J = 54.40 Hz, 1H), 7.20-7.27(m, 3H). A6 3.41 ¹H NMR (300 MHz, CHCl₃-d): ppm 0.65-0.66 (m, 4H), 1.21(t, 3H), 2.62 (q, 2H), 2.64 (bs, 1H), 3.81 (s, 3H), 4.71 (s, 2H), 6.86(t, J = 54.6 Hz, 1H), 6.89-6.95 (m, 2H), 7.13-7.18 (m, 1H). A7 3.70 ¹HNMR (300 MHz, CHCl₃-d): ppm 0.65-0.69 (m, 4H), 1.22 (d, 6H), 2.69 (bs,1H), 3.10-3.14 (m, 1H), 3.81 (s, 3H), 4.75 (s, 2H), 6.86 (t, J = 54.6Hz, 1H), 6.88-6.93 (m, 2H), 7.23-7.28 (m, 1H). A8 3.46 ¹H NMR (300 MHz,CHCl₃-d): ppm 0.60-0.66 (m, 6H), 0.89-0.95 (m, 2H), 1.82-1.84 (m, 1H),2.73 (bs, 1H), 3.81 (s, 3H), 4.89 (s, 2H), 6.68-6.99 (m, 4H). A9 4.21 ¹HNMR (300 MHz, CHCl₃-d): ppm 0.64-0.68 (m, 4H), 1.56-1.62 (m, 2H),1.62-1.70 (m, 2H), 1.76-1.83 (m, 2H), 1.96-2.05 (m, 2H), 2.71 (bs, 1H),3.13-3.19 (m, 1H), 3.81 (s, 3H), 4.76 (s, 2H), 6.86 (t, J = 54.0 Hz,1H), 6.87-6.97 (m, 2H), 7.23-7.28 (m, 1H). A10 3.65 ¹H NMR (400 MHz,CHCl₃-d): ppm 0.65 (bs, 4H), 1.21 (d, J = 6.75 Hz, 5H), 2.29-2.59 (m,1H), 3.00-3.36 (m, 1H), 3.79 (s, 3H), 4.83 (s, 2H), 6.68-7.06 (m, 2H),7.13 (d, J = 7.78 Hz, 1H), 7.27-7.33 (m, 1H). A11 3.70 ¹H NMR (500 MHz,CHCl₃-d): ppm 0.65 (bs, 4H), 2.31 (s, 3H), 2.64 (m, 1H), 3.81 (s, 3H),4.73 (bs, 2H), 6.89 (t, J = 54.6 Hz, 1H), 7.01-7.14 (m, 3H). A12 3.99 ¹HNMR (500 MHz, CHCl₃-d): ppm 0.66 (bs, 4H), 1.22 (d, J = 6.97 Hz, 6H),2.31 (s, 3H), 2.54-2.75 (m, 1H), 2.99-3.25 (m, 1H), 3.81 (s, 3H), 4.75(bs, 2H), 6.89 (t, J = 53.90 Hz, 1H), 7.01-7.23 (m, 3H). A13 3.76 ¹H NMR(500 MHz, CHCl₃-d): ppm 0.61-0.68 (m, 6H), 0.80-1.00 (m, 2H), 1.74-2.00(m, 1H), 2.31 (s, 3H), 2.53-2.82 (m, 1H), 3.81 (s, 3H), 4.89 (bs, 2H),6.83 (t, J = 54.80 Hz, 1H), 6.91-7.06 (m, 3H). A14 4.36 ¹H NMR (500 MHz,CHCl₃-d): ppm 0.62 (m, 4H), 1.44 (s, 9H), 2.28 (s, 3H), 2.74-3.02 (m,1H), 3.83 (bs, 3H), 5.02 (bs, 2H), 6.85 (t, J = 54.40 Hz, 1 H), 7.01(bs, 1H), 7.21-7.29 (m, 2 H). A15 3.80 ¹H NMR (500 MHz, CHCl₃-d): ppm0.50-0.67 (m, 4H), 2.81 (bs, 1H), 3.78 (s, 3H), 4.85 (bs, 2H), 6.78 (t,J = 55.00 Hz, 1H), 7.20-7.29 (m, 2H), 7.54 (d, J = 8.17 Hz, 1H). A163.78 ¹H NMR (500 MHz, CHCl₃-d): ppm 0.55-0.70 (m, 4H), 2.37 (s, 3H),2.72-3.04 (m, 1H), 3.83 (bs, 3H), 4.91 (bs, 2H), 6.86 (t, J = 54.50 Hz,1H), 7.10-7.20 (m, 2H), 7.54 (d, J = 7.89 Hz, 1H). A17 3.46 ¹H NMR (500MHz, CHCl₃-d): ppm 0.47-0.64 (m, 4H), 2.29-2.55 (m, 1H), 3.80 (s, 3H),5.05 (s, 2H), 6.95 (t, J = 54.40 Hz, 1H), 7.40 (t, J = 7.86 Hz, 1H),7.60-7.70 (dd, 2H). A18 3.62 ¹H NMR (500 MHz, CHCl₃-d): ppm 0.50-0.74(m, 4H), 2.45-2.71 (m, 1H), 3.81 (s, 3H), 4.99 (s, 2H), 6.91 (t, J =54.40 Hz, 1H), 7.45-7.57 (m, 2H). A19 4.04 ¹H NMR (500 MHz, CHCl₃-d):ppm 0.65 (bs, 4H), 1.20 (t, J = 7.43 Hz, 3H), 2.22 (s, 3H), 2.24 (s,3H), 2.58-2.64 (m, 2H), 3.80 (s, 3H), 4.70 (bs, 2H), 6.89 (t, J = 54.70Hz, 3H), 6.98 (bs, 2H). A20 4.36 ¹H NMR (500 MHz, CHCl₃-d): ppm0.55-0.84 (m, 4H), 1.27 (d, J = 6.97 Hz, 6H), 2.73-2.85 (m, 1H),3.04-3.23 (m, 1H), 3.80 (s, 3H), 4.60-5.06 (m, 1H), 6.99-7.38 (m, 5H).

The advanced fungicidal activity of the active compound combinationsaccording to the invention is evident from the example below. While theindividual active compounds exhibit weaknesses with regard to thefungicidal activity, the combinations have an activity which exceeds asimple addition of activities.

The advanced fungicidal activity of the active compound combinationsaccording to the invention is evident from the example below. While theindividual active compounds exhibit weaknesses with regard to thefungicidal activity, the combinations have an activity which exceeds asimple addition of activities.

A synergistic effect of fungicides is always present when the fungicidalactivity of the active compound combinations exceeds the total of theactivities of the active compounds when applied individually. Theexpected activity for a given combination of two active compounds can becalculated as follows (cf. Colby, S. R., “Calculating Synergistic andAntagonistic Responses of Herbicide Combinations”, Weeds 1967, 15,20-22):

If

-   X is the efficacy when active compound A is applied at an    application rate of m ppm (or g/ha),-   Y is the efficacy when active compound B is applied at an    application rate of n ppm (or g/ha),-   E is the efficacy when the active compounds A and B are applied at    application rates of m and n ppm (or g/ha), respectively, and    then

$E = {X + Y - \frac{X \cdot Y}{100}}$

The degree of efficacy, expressed in % is denoted. 0% means an efficacywhich corresponds to that of the control while an efficacy of 100% meansthat no disease is observed.

If the actual fungicidal activity exceeds the calculated value, then theactivity of the combination is superadditive, i.e. a synergistic effectexists. In this case, the efficacy which was actually observed must begreater than the value for the expected efficacy (E) calculated from theabovementioned formula.

A further way of demonstrating a synergistic effect is the method ofTammes (cf. “Isoboles, a graphic representation of synergism inpesticides” in Neth. J. Plant Path., 1964, 70, 73-80).

The invention is illustrated by the following examples. However theinvention is not limited to the examples.

EXAMPLE A Alternaria Test (Tomatoes)/Preventive

-   Solvent: 24.5 parts by weight of acetone    -   24.5 parts by weight of dimethylacetamide-   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound at the stated rate of application. Afterthe spray coating has dried on, the plants are inoculated with anaqueous spore suspension of Alternaria solani. The plants are thenplaced in an incubation cabinet at approximately 20° C. and a relativeatmospheric humidity of 100%.

The test is evaluated 3 days after the inoculation. 0% means an efficacywhich corresponds to that of the untreated control while an efficacy of100% means that no disease is observed. The table below clearly showsthat the observed activity of the active compound combination accordingto the invention is greater than the calculated activity, i.e. asynergistic effect is present.

TABLE A1 Alternaria test (tomatoes)/preventive Application rate ofactive compound in Efficacy in % Active compounds ppm a.i. found*calc.** (A5) N-(5-chloro-2- 1 30 isopropylbenzyl)-N- 0.5 38cyclopropyl-3- (difluoromethyl)-5-fluoro-1- methyl-1H-pyrazole-4-carboxamide (b39) N-(4-chloro-2,6- 1 17 difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl- 1H-pyrazol-5-amine (b40)2-[4-(4-chlorophenoxy)-2- 2.5 66 (trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan- 2-ol (A5) + 1:1 1 + 1 49 42 (b39) (A5) +1:2.5   1 + 2.5 95 76 (b40) (A5) + 1:5 0.5 + 2.5 90 79 (b40) *found =activity found **calc. = activity calculated using Colby's formula

TABLE A2 Alternaria test (tomatoes)/preventive Application rate ofactive compound in Efficacy in % Active compounds ppm a.i. found*calc.** (A5) N-(5-chloro-2- 1 41 isopropylbenzyl)-N- 0.5 0cyclopropyl-3- (difluoromethyl)-5- fluoro-1-methyl-1H- pyrazole-4-carboxamide (b45) 9-fluoro-2,2-dimethyl-5- 0.5 24 (quinolin-3-yl)-2,3-dihydro-1,4- benzoxazepine (b46) 2-{2-fluoro-6-[(8-fluoro- 1 242-methylquinolin-3- 0.5 18 yl)oxy]phenyl}propan-2-ol (b47)2-{2-[(7,8-difluoro-2- 1 29 methylquinolin-3- 0.5 9 yl)oxy]-6-fluorophenyl}propan-2-ol (A5) + 1:0.5 1 + 0.5 65 55 (b45) (A5) + 1:0.51 + 0.5 76 52 (b46) (A5) + 1:2 0.5 + 1   76 24 (b46) (A5) + 1:0.5 1 +0.5 74 46 (b47) (A5) + 1:2 0.5 + 1   62 29 (b47) *found = activity found**calc. = activity calculated using Colby's formula

EXAMPLE B Botrytis Test (Beans)/Preventive

-   Solvent: 24.5 parts by weight of acetone    -   24.5 parts by weight of dimethylacetamide-   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound. After the spray coating has dried on, 2small pieces of agar covered with growth of Botrytis cinerea are placedon each leaf. The inoculated plants are placed in a darkened chamber at20° C. and a relative atmospheric humidity of 100%.

2 days after the inoculation, the size of the lesions on the leaves isevaluated. 0% means an efficacy which corresponds to that of theuntreated control, while an efficacy of 100% means that no disease isobserved. The table below clearly shows that the observed activity ofthe active compound combination according to the invention is greaterthan the calculated activity, i.e. a synergistic effect is present.

TABLE B1 Botrytis test (beans)/preventive Application rate of activecompound in Efficacy in % Active compounds ppm a.i. found* calc.** (A5)N-(5-chloro-2- 1 15 isopropylbenzyl)-N- cyclopropyl-3-(difluoromethyl)-5-fluoro-1- methyl-1H-pyrazole-4- carboxamide (b27)3-(4,4-difluoro-3,3-dimethyl- 1 60 3,4-dihydroisoquinolin-1-yl)quinoline (b41) 2-[4-(4-chlorophenoxy)-2- 10 36(trifluoromethyl)phenyl]-1- (1H-1,2,4-triazol-1-yl)butan- 2-ol (A5) +1:1 1 + 1  98 66 (b27) (A5) + 1:10 1 + 10 74 46 (b41) *found = activityfound **calc. = activity calculated using Colby's formula

EXAMPLE C Pyrenophora teres-Test (Barley)/Preventive

-   Solvent: 49 parts by weight of N,N-dimethylacetamide-   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound or active compound combination at thestated rate of application. After the spray coating has been dried, theplants are sprayed with a spore suspension of Pyrenophora teres. Theplants remain for 48 hours in an incubation cabinet at approximately 20°C. and a relative atmospheric humidity of approximately 100%. The plantsare placed in the greenhouse at a temperature of approximately 20° C.and a relative atmospheric humidity of approximately 80%.

The test is evaluated 8 days after the inoculation. 0% means an efficacywhich corresponds to that of the untreated control, while an efficacy of100% means that no disease is observed. The table below clearly showsthat the observed activity of the active compound combination accordingto the invention is greater than the calculated activity, i.e. asynergistic effect is present.

TABLE C1 Pyrenophora teres-test (barley)/preventive Application rate ofactive compound in Efficacy in % Active compounds ppm a.i. found*calc.** (A5) N-(5-chloro-2- 10 13 isopropylbenzyl)-N- cyclopropyl-3-(difluoromethyl)-5-fluoro-1- methyl-1H-pyrazole-4- carboxamide (b27)3-(4,4-difluoro-3,3-dimethyl- 240 75 3,4-dihydroisoquinolin-1- 60 38yl)quinoline (b41) 2-[4-(4-chlorophenoxy)-2- 60 0(trifluoromethyl)phenyl]-1- 15 25 (1H-1,2,4-triazol-1-yl)butan- 2-ol(A5) + 1:24  10 + 240 100 78 (b27) (A5) + 1:6 10 + 60 75 46 (b27) (A5) +1:6 10 + 60 88 13 (b41) (A5) + 1:1.5 10 + 15 88 35 (b41) *found =activity found **calc. = activity calculated using Colby's formula

EXAMPLE D Septoria tritici-Test (Wheat)/Preventive

-   Solvent: 49 parts by weight of N,N-dimethylacetamide-   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound or active compound combination is mixed with thestated amounts of solvent and emulsifier, and the concentrate is dilutedwith water to the desired concentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound or active compound combination at thestated rate of application. After the spray coating has been dried, theplants are sprayed with a spore suspension of Septoria tritici. Theplants remain for 48 hours in an incubation cabinet at approximately 20°C. and a relative atmospheric humidity of approximately 100% andafterwards for 60 hours at approximately 15° C. in a translucentincubation cabinet at a relative atmospheric humidity of approximately100%. The plants are placed in the greenhouse at a temperature ofapproximately 15° C. and a relative atmospheric humidity ofapproximately 80%.

The test is evaluated 21 days after the inoculation. 0% means anefficacy which corresponds to that of the untreated control, while anefficacy of 100% means that no disease is observed. The table belowclearly shows that the observed activity of the active compoundcombination according to the invention is greater than the calculatedactivity, i.e. a synergistic effect is present.

TABLE D1 Septoria tritici-test (wheat)/preventive Application rate ofactive compound in Efficacy in % Active compounds ppm a.i. found*calc.** (A5) N-(5-chloro-2- 10 50 isopropylbenzyl)-N- 5 50cyclopropyl-3- (difluoromethyl)-5-fluoro-1- methyl-1H-pyrazole-4-carboxamide (b29) 3-(difluoromethyl)-N- 5 94 methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propan- 2-yl]-1H-pyrazole-4- carboxamide (b39)N-(4-chloro-2,6- 240 88 difluorophenyl)-4-(2-chloro- 60 504-fluorophenyl)-1,3-dimethyl- 1H-pyrazol-5-amine (A5) + 1:0.5 10 + 5 100 97 (b29) (A5) + 1:1 5 + 5 100 97 (b29) (A5) + 1:24  10 + 240 100 94(b39) (A5) + 1:6 10 + 60 94 75 (b39) *found = activity found **calc. =activity calculated using Colby's formula

TABLE D2 Septoria tritici-test (wheat)/preventive Application rate ofactive compound in Efficacy in % Active compounds ppm a.i. found*calc.** (A5) N-(5-chloro-2- 20 67 isopropylbenzyl)-N- 10 17cyclopropyl-3- (difluoromethyl)-5- fluoro-1-methyl-1H- pyrazole-4-carboxamide (b45) 9-fluoro-2,2-dimethyl-5- 200 0 (quinolin-3-yl)-2,3- 500 dihydro-1,4- benzoxazepine (b46) 2-{2-fluoro-6-[(8-fluoro- 200 672-methylquinolin-3- 50 0 yl)oxy]phenyl}propan-2-ol (b47)2-{2-[(7,8-difluoro-2- 200 67 methylquinolin-3- 50 0 yl)oxy]-6-fluorophenyl}propan-2-ol (A5) + 1:20  10 + 200 92 17 (b45) (A5) + 1:2.520 + 50 92 67 (b45) (A5) + 1:20  10 + 200 92 73 (b46) (A5) + 1:2.5 20 +50 92 67 (b46) (A5) + 1:20  10 + 200 100 73 (b47) (A5) + 1:2.5 20 + 50100 67 (b47) *found = activity found **calc. = activity calculated usingColby's formula

EXAMPLE E Sphaerotheca Test (Cucumbers)/Preventive

-   Solvent: 24.5 parts by weight of acetone    -   24.5 parts by weight of dimethylacetamide-   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound at the stated rate of application. Afterthe spray coating has dried on, the plants are inoculated with anaqueous spore suspension of Sphaerotheca fuliginea. The plants are thenplaced in a greenhouse at approximately 23° C. and a relativeatmospheric humidity of approximately 70%.

The test is evaluated 7 days after the inoculation. 0% means an efficacywhich corresponds to that of the untreated control, while an efficacy of100% means that no disease is observed. The table below clearly showsthat the observed activity of the active compound combination accordingto the invention is greater than the calculated activity, i.e. asynergistic effect is present.

TABLE E1 Sphaerotheca test (cucumbers)/preventive Application rate ofactive compound in Efficacy in % Active compounds ppm a.i. found*calc.** (A5) N-(5-chloro-2- 1 37 isopropylbenzyl)-N- 0.5 30cyclopropyl-3- (difluoromethyl)-5- fluoro-1-methyl-1H- pyrazole-4-carboxamide (b29) 3-(difluoromethyl)-N- 1 30 methoxy-1-methyl-N-[1- 0.2530 (2,4,6-trichlorophenyl)propan- 2-yl]-1H-pyrazole-4- carboxamide (b40)2-[4-(4-chlorophenoxy)-2- 10 85 (trifluoromethyl)phenyl]-1- 2.5 37(1H-1,2,4-triazol-1-yl)propan- 2-ol (A5) + 1:1 1 + 1 73 56 (b29) (A5) +1:0.25   1 + 0.25 63 56 (b29) (A5) + 1:2.5   1 + 2.5 70 60 (b40) (A5) +1:5 0.5 + 10  97 90 (b40) *found = activity found **calc. = activitycalculated using Colby's formula

EXAMPLE F Venturia Test (Apples)/Preventive

-   Solvent: 24.5 parts by weight of acetone    -   24.5 parts by weight of dimethylacetamide-   Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with water to the desiredconcentration.

To test for preventive activity, young plants are sprayed with thepreparation of active compound at the stated rate of application. Afterthe spray coating has dried on, the plants are inoculated with anaqueous conidia suspension of the causal agent of apple scab (Venturiainaequalis) and then remain for 1 day in an incubation cabinet atapproximately 20° C. and a relative atmospheric humidity of 100%. Theplants are then placed in a greenhouse at approximately 21° C. and arelative atmospheric humidity of approximately 90%.

The test is evaluated 10 days after the inoculation. 0% means anefficacy which corresponds to that of the untreated control, while anefficacy of 100% means that no disease is observed. The table belowclearly shows that the observed activity of the active compoundcombination according to the invention is greater than the calculatedactivity, i.e. a synergistic effect is present.

TABLE F1 Venturia test (apples)/preventive Application rate of activecompound in Efficacy in % Active compounds ppm a.i. found* calc.** (A5)N-(5-chloro-2- 1 0 isopropylbenzyl)-N- 0.5 0 cyclopropyl-3-(difluoromethyl)-5- fluoro-1-methyl-1H- pyrazole-4- carboxamide (b27)3-(4,4-difluoro-3,3-dimethyl- 0.5 23 3,4-dihydroisoquinolin-1-yl)quinoline (A5) + 1:0.5   1 + 0.5 78 23 (b27) (A5) + 1:1 0.5 + 0.5 9023 (b27) *found = activity found **calc. = activity calculated usingColby's formula

TABLE F2 Venturia test (apples)/preventive Application rate of activecompound in Efficacy in % Active compounds ppm a.i. found* calc.** (A5)N-(5-chloro-2- 2 29 isopropylbenzyl)-N- 1 0 cyclopropyl-3- 0.5 0(difluoromethyl)-5- fluoro-1-methyl-1H- pyrazole-4- carboxamide (b45)9-fluoro-2,2-dimethyl-5- 1 0 (quinolin-3-yl)-2,3- dihydro-1,4-benzoxazepine (b46) 2-{2-fluoro-6-[(8-fluoro- 0.5 18 2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol (b47) 2-{2-[(7,8-difluoro-2- 0.5 30methylquinolin-3- yl)oxy]-6- fluorophenyl}propan-2-ol (A5) + 1:1 1 + 1  85 0 (b45) (A5) + 1:2 0.5 + 1   72 0 (b45) (A5) + 1:0.25 2 + 0.5 93 42(b46) (A5) + 1:1 0.5 + 0.5  71 18 (b46) (A5) + 1:0.25 2 + 0.5 78 50(b47) (A5) + 1:0.5 1 + 0.5 64 30 (b47) *found = activity found **calc. =activity calculated using Colby's formula

The invention claimed is:
 1. An active compound composition comprising(A)N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamideor an agrochemically acceptable salt thereof, and (B) an activefungicidal compound B selected from the group consisting of (b27)3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline;(b29) 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propan-2-yl]-1H-pyrazole-4-carboxamide; (b40)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol;(b41)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol;(b45)9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine;(b46)2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol;and (b47)2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol;wherein if (B) is (b27), (b29), (b45), (b46) or (b47), (A) and (B) arepresent in a weight ratio in a range of 10:1 to 1:50; and wherein if (B)is (b40) or (b41), (A) and (B) are present in a weight ratio in a rangeof 1:1 to 1:50.
 2. A composition for controlling phytopathogenic harmfulfungi, comprising the active compound composition according to claim 1,and further comprising extenders and/or surfactants.
 3. The compositionfor controlling phytopathogenic harmful fungi according to claim 2comprising at least one further active ingredient selected from thegroup of insecticides, attractants, sterilants, bactericides,acaricides, nematicides, fungicides, growth regulators, herbicides,fertilizers, safeners and semiochemicals.
 4. A method for controllingphytopathogenic harmful fungi, comprising applying the active compoundcomposition according to claim 1 to the phytopathogenic harmful fungiand/or their habitat.
 5. A process for producing compositions forcontrolling phytopathogenic harmful fungi, comprising mixing the activecompound composition according to claim 1 with extenders and/orsurfactants.
 6. A method for controlling phytopathogenic harmful fungi,comprising applying the active compound composition according to claim 1to a transgenic plant.
 7. A method for controlling phytopathogenicharmful fungi, comprising applying the active compound compositionaccording to claim 1 to a seed or to a seed of a transgenic plant. 8.active compound composition according to claim 1, wherein the fungicidalcompound B is (b27)3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl) quinoline. 9.The active compound composition according to claim 1, wherein if (B) is(b27), (b29), (b45), (b46) or (b47), (A) and (B) are present in asynergistically effective weight ratio in a range of 4:1 to 1:25; andwherein if (B) is (b40) or (b41), (A) and (B) are present in asynergistically effective weight ratio in a range of 1:1 to 1:25. 10.The active compound composition according to claim 8, wherein (A) and(B) are present in a synergistically effective weight ratio in a rangeof 2:1 to 1:25.
 11. The active compound composition according to claim1, wherein the fungicidal compound B is (b29)3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propan-2-yl]-1H-pyrazole-4-carboxamide.12. The active compound composition according to claim 1, wherein thefungicidal compound B is (b40)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol.13. The active compound composition according to claim 1, wherein thefungicidal compound B is (b41)2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol.14. The active compound composition according to claim 1, wherein thefungicidal compound B is (b45) 9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine.
 15. The active compoundcomposition according to claim 1, wherein the fungicidal compound B is(b46)2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol.16. The active compound composition according to claim 1, wherein thefungicidal compound B is (b47)2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol.17. The active compound composition according to claim 1, wherein (A)and (B) are the only active compounds.
 18. The active compoundcomposition according to claim 11, wherein (A) and (B) are present in asynergistically effective weight ratio in a range of 2:1 to 1:1.
 19. Theactive compound composition according to claim 12, wherein (A) and (B)are present in a synergistically effective weight ratio in a range of1:2 to 1:5.
 20. The active compound composition according to claim 13,wherein (A) and (B) are present in a synergistically effective weightratio in a range of 1:1 to 1:10.
 21. The active compound compositionaccording to claim 14, wherein (A) and (B) are present in asynergistically effective weight ratio in a range of 1:1 to 1:20. 22.The active compound composition according to claim 15, wherein (A) and(B) are present in a synergistically effective weight ratio in a rangeof 4:1 to 1:20.
 23. The active compound composition according to claim16, wherein (A) and (B) are present in a synergistically effectiveweight ratio in a range of 4:1 to 1:20.